Ex Parte Argyropoulos et al

Patent Trial and Appeal Board

Dec 12, 2016

11939420 (P.T.A.B. Dec. 12, 2016)

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.
11/939,420 11/13/2007 John N. Argyropoulos 65267A-US-NP 4699
78693 7590 12/14/2016
The TT Salazar T aw Firm PT T C EXAMINER
1934 W. Gray
Suite 401
FEELY, MICHAEL J
Houston, TX 77019 ART UNIT PAPER NUMBER
1766
NOTIFICATION DATE DELIVERY MODE
12/14/2016 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
following e-mail address(es):
jls@jlsalazar.com
paralegal@jlsalazar.com
mail@ salazarip.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte JOHN N. ARGYROPOULOS,
DEBKUMAR BHATTACHARJEE, and RAJESH TURAKHIA
Appeal 2015-004687
Application 11/939,420
Technology Center 1700
Before PETER F. KRATZ, DONNA M. PRAISS, and LILAN REN,
Administrative Patent Judges.
PRAISS, Administrative Patent Judge.
DECISION ON APPEAL1
This is a decision on an appeal under 35 U.S.C. § 134 from the
Examiner’s final rejection of claims 1—14. We have jurisdiction pursuant to
35 U.S.C. § 6. We affirm.
1 In this decision we refer to the Specification filed November 13, 2007
(“Spec.”), the drawings filed February 1, 2008 (“Fig.”), the Final Office
Action mailed May 28, 2013 (“Final Act.”), the Appeal Brief filed
November 26, 2013 (“Br.”), and the Examiner’s Answer mailed January 13,
2014 (“Ans.”).
Appeal 2015-004687
Application 11/939,420
Appellants’2 claimed invention is directed to a curable formulation
that contains a hardener composition and an epoxy resin wherein no
accelerator is present in the curable formulation and the formulation is
capable of certain properties. The claimed invention is also directed to (1) a
method for adhering two substrates by applying the curable formulation to
one or both substrates and bringing the substrates into a contacting
relationship and (2) a method for coating a substrate by applying a coating
composition that includes the curable formulation and curing it. According
to Appellants, the claimed curable formulation and its properties are
reflected in Example 4 of the Specification. Br. 3^4. The reactivity of the
Example 4 mixtures “is measured as percent conversion at room
temperature” using a Differential Scanning Calorimeter (DSC) that monitors
enthalpy during the curing reaction. Spec. 1102. The results are shown in
Figure 1 below:
Conversion at Room Temperature
FIG. 1
2 Appellants identify the real party in interest as Dow Global Technologies,
Inc., a wholly-owned subsidiary of Dow Chemical. Br. 2.
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Application 11/939,420
Figure 1 shows the percent conversion at room temperature over time in
hours. Id. Fracture toughness of the samples is shown in Figure 2 below.
Id. 1103.
£* 1.0000
s 0.9000
& 0.8000
7* 0.7000
^ 0,8000
| 0.5000
Jl 0.400005
g 0.3000
g 0,2000
| 0.1000
(S 0.0000
Fracture Toughness Comparison
F/a 2
Figure 2 is a comparison of the Example 4 embodiment to the prior art.
Id. 114.
Claims 1,9, 13, and 14 are illustrative and reproduced below:
1. A curable formulation consisting essentially of:
a hardener composition comprising:
(a) l,3-bis(aminomethyl)cyclohexane; and
(b) l,4-bis(aminomethyl)cyclohexane; and
an epoxy resin;
wherein no accelerator is present in the curable formulation and
the curable formulation is capable of curing at room temperature
in not more than about 5 hours in the absence of an accelerator
to a level of at least 70% conversion.
9. A method for adhering two substrates, comprising:
applying curable formulation of claim 1 to one or both of the
substrates; and
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Application 11/939,420
bringing the substrates into a contacting relationship.
13. A method for coating a substrate, comprising:
applying a coating composition to a substrate;
wherein the coating composition includes the curable
formulation of claim 1;
curing the curable formulation at room temperature in not more
than about 5 hours to a level of at least 70% conversion, wherein
such curing occurs in the absence of an accelerator.
14. A curable formulation consisting essentially of:
a hardener composition comprising:
(a) l,3-bis(aminomethyl)cyclohexane; and
(b) l,4-bis(aminomethyl)cyclohexane; and
an epoxy resin;
wherein no accelerator is present in the curable formulation and
the curable formulation is capable of curing at room temperature
in not more than about 5 hours in the absence of an accelerator
to a level of at least 70% conversion, such that a 1/8 inch clear
casting sample made from the curable formulation exhibits a
fracture toughness of at least 0.7 MPa*m 1/2 when tested in
accordance with ASTM D5045.
The Examiner maintains the following grounds of rejection.3
Claims 1—14 stand rejected under 35 U.S.C. § 112, first paragraph, for
failing to comply with the written description requirement. Claims 1—8 and
14 stand rejected under 35 U.S.C. § 103(a) as being unpatentable over
3 The Examiner withdrew the rejection of claims 1—14 under 35 U.S.C.
§ 112(b), second paragraph, as being indefinite. Ans. 10.
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Application 11/939,420
Tulchinsky.4 Claims 9—13 stand rejected under 35 U.S.C. § 103(a) as being
unpatentable over Tulchinsky in view of Marten5 and Cameron.6
We affirm the stated rejections. Our reasons follow.
Written Description
Concerning the written description rejection of the claims, the
Examiner refers to the additional samples in Example 5 for which actual
data points are provided in the Specification. Specifically, the Examiner
finds that Table 10 supports percent conversion measurements taken at 5
hours for the curable formulation, but it does not support measurements
taken at “about 5 hours” as recited in claims 1,13, and 14. Ans. 2—3. The
Examiner also finds that Table 10 supports 70.4, 70.5, and 71.6 percent
conversions at 5 hours, but “it does not support the end point of 70%
conversion or the full range of at least 70% conversion’’ as recited in claims
1,13, and 14. Id. Additionally, the Examiner finds that fracture toughness
of “at least 0.7 MPa*m1/2” recited in claim 14 is not supported by Figure 3,
which includes toughness values of 0.9854, 0.7247, 0.7173, and 0.8646
MPa*m1/2. Id. at 3.
Appellants contend that the rejection is in error because “[b]y
focusing on the details of specific numbers in Appellants’ Examples and
Tables, the Examiner reads these specific numbers into the claims.” Br. 7.
According to Appellants, when the claims are read in light of the whole
specification, “Figure 1 includes not only the specific ‘% conversion vs.
4 Tulchinsky et al., WO 2007/005594 A2, published Jan. 11, 2007
(“Tulchinsky”).
5 Marten et al., US 4,481,349, issued Nov. 6, 1984 (“Marten”).
6 Cameron et al., US 6,576,297 Bl, issued June 10, 2003 (“Cameron”).
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Application 11/939,420
Time’ data points plotted for Sample 4, but, by interpolation, other %
conversions at other times for Sample 4, as well as for Comparative Sample
4.” Id. at 8. Appellants further assert that “[n]or would a person of ordinary
skill in the art take the literal, specific numerical values of fracture toughness
plotted in Figure 3 as the invention.”
The Examiner responds that the limited data in Table 10 fails to
support the full range of “at least 70%” and that the data used to generate
Figure 1 is not disclosed. Ans. 10—11. The Examiner further responds that
the data used to generate Figure 2 is not disclosed and the fracture toughness
values in Figure 3 do not support the full range of “at least 0.7MPa*m12”
which includes all values higher than 0.7 MPa*m12. Id. at 11.
Appellants argue the claims together. Br. 6—9. Therefore, we confine
our discussion to claims 1 and 14, which we select as representative. Claims
2—13 stand or fall with claim 1 from which they depend. See 37 C.F.R.
§ 41.37(c)(l)(iv). Claim 14 contains all of the limitations of claim 1 plus the
toughness property of a cast sample. Br. 5. We agree with the Examiner
that neither Table 10 nor Figures 1 and 3 provide written description support
for the full scope of claims 1 and 14. Table 10 provides data for Example 5
involving Samples 5, 6, 7, 8, and 9 and Comparative Sample 5, the
composition of which is shown in Tables 8 and 9, while Figure 1 concerns
Example 4 involving Sample 4 and Comparative Sample 4, the composition
of which is shown in Table 7. Spec. 104—106, 100-102. Tables 7, 8, and
9 are shown below.
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Appeal 2015-004687
Application 11/939,420
.Raw Materials 1 Comparative Sample 4 Sample 4 !
D.E.R/331 | 84.1 wt,% :
IPDA 18.2 wt%
UNOXOL diamine | 15 J wi%
Table 8
Product DC! DC2 DC3 DC4
UNOXOL® mrnrnm (wl %) 99.8 97 89,4 75 J
3*azj.bieycio|3.3.1]nonan®:"" 1JA (wt, %) — — 3.4 0.3
3-azabicyel0t33, 1 ^aon-2-eoe - B1 (wt %) — 1 2 14,5
< 1 lrion.tn~2-am.ine - BDA (wt, %) — 2 1.8 9.1
_-r.-T.-_-T.....................
Table 9
| Raw Materials 1
1 I
Comparative
Sample 5
Sample 3 Sample 6 j Sample 7 Samples J
| D.E.R, 331 | 81.47 84. i 3 84,13 | 82,86 81,17
! IPDA j 18.43 — — j
| DC! | 15,87- «-»
] DC2 | — ................ J 15.87
DC3 | — 17.14 l
I D04 | — ... — 18,83 1
Spec. 11 101, 105, 106.
According to the Specification, UNOXOL diamine is an amine curing
agent mixture including the cis and trans isomers of 1,3- and 1,4-
bis(aminomethyl)cyclohexane required by the claims. Id. 192. IPDA is
isophorone diamine. Id. D.E.R. 331 is bisphenol A liquid epoxy resin. Id.
1 63. The Specification further identifies bisphenol A as useful for forming
a resin {id. 1 57) and as an accelerator {id. 143). Therefore, each of samples
4—8, including the comparative samples, use the same resin (a bisphenol A
resin). The difference between sample 4 and samples 5—8 is the presence of
impurities in samples 5—8 that cause “no significant difference in the
reaction rate” of the formulations. Id. 1107. Claims 1 and 14 are not
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Application 11/939,420
limited to the bisphenol A resin of the samples, but, rather, broadly recite
“an epoxy resin.” The Specification evidences that there is a great variety of
epoxy resins. Id. 50—65.
Given the limited samples and data, we are not persuaded that
Appellants have shown that the full ranges for “capable of curing at room
temperature in not more than about 5 hours in the absence of an accelerator
to a level of at least 70% conversion” recited in claims 1 and 14 are
supported by samples 4 through 8. Additionally, the claimed “at least 70%
conversion” encompasses the range of 70% conversion and greater,
however, the data may only support a numerical value that is about 70% for
the specific samples identified in the Specification. Sample 8, which has a
conversion of 68%, does not support “at least 70%” and the remaining
samples do not support the full scope of the range between 70% and 100%
conversion. “Adequate written description means that the applicant, in the
specification, must ‘convey with reasonable clarity to those skilled in the art
that, as of the filing date sought, he or she was in possession of the [claimed]
invention.’” Agilent Techs., Inc. v. Affymetrix, Inc., 567 F.3d 1366, 1379
(Fed. Cir. 2009). Because the samples identified by Appellants do not
convey that the breadth of the extent of conversion when curing at room
temperature was in applicants’ possession at about 5 hours or less for an
epoxy resin other than a bisphenol A resin, let alone the full range of epoxy
resins claimed, we are not persuaded that the Examiner erred in rejecting
claims 1—14 for lacking written description support.
Similarly, we are not persuaded that samples 4—9 provide written
description support for the full scope of the fracture toughness property
recited in claim 14. While Figure 2 shows the fracture toughness of the
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Application 11/939,420
samples of Example 4 (Spec. 1103), Figure 3, below, is said to show the
fracture toughness of the samples of Example 5 {id. 129).
Figure 3 compares the fracture toughness of the Example 5 bisphenol A
epoxy resin compositions to an epoxy resin cured with IPDA (comparative
sample 5). Spec. Tflf 15, 111. Because the samples that include a hardener
composition comprising 1,3- and 1,4-bis(aminomethyl)cyclohexane as
recited in claim 14 do not convey that the breadth of the fracture toughness
claimed was in applicants’ possession for an epoxy resin other than a
bisphenol A resin, let alone the full range of epoxy resins claimed, we also
are not persuaded that the Examiner erred in rejecting claim 14 for lacking
written description support
Obviousness
Regarding the rejection of claim 1 over Tulchinsky, the Examiner
finds that Tulchinsky discloses that “bis(aminomethyl)cyclohexanes can be
used as an epoxy curing agent” and that Tulchinsky’s “silence [regarding the
presence (or non-presence) of an accelerator] suggests that one is not present
in their suggested curable formulation” or “[a]t the very least, their silence
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Application 11/939,420
suggests that an accelerator is not required (optional) in their suggested
curable formulation.” Ans. 4—5 (citing Tulchinsky 1, 14). The Examiner
further finds that because Tulchinsky suggests a formulation that features the
“essential components” of claim 1, namely, bis(aminomethyl)cyclohexanes
corresponding to (a) and (b) and an epoxy resin, it “is identical or nearly
identical to the experimental formulations set forth in the instant
specification, particularly ‘Sample 5’.” As such, the Examiner finds that the
properties required by claim 1 are necessarily present because a chemical
composition and its properties are inseparable. Id. at 5—6.
Appellants contend that the Examiner erred in rejecting claim 1 over
Tulchinsky because “Tulchinsky et al. is silent on everything regarding
curable formulations including an epoxy resin and curing them.” Br. 15.
Appellants assert that the rejection over Tulchinsky “is pure speculation”
because “Tulchinsky et al. do not state that an accelerator is not included.”
Id. at 16. According to Appellants, Tulchinsky therefore discloses “the
entire universe of possible compositions comprising of epoxy resin and
diamine curatives.” Id. Appellants further argue that “there is no teaching,
suggestion or expectation of success evidence from Tulchinsky et al. that
this would lead to a curable formulation capable of curing at room
temperature in not more than about 5 hours in the absence of an accelerator
to a level of at least 70% conversion, or such that a 1/8 inch clear casting
sample made from the curable formulation exhibits a fracture toughness of at
least 0.7 MPa*m1/2 when tested in accordance with ASTM D5045.” Id. at
18. Additionally, Appellants assert that “there is no suggestion or
motivation ... to modify the teachings of Tulchinsky et al. to require the
above-mentioned elements.” Id. at 18—19. Appellants assert that Tulchinsky
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merely invites experimentation to find the claimed species because the
Examiner has not shown that the absence of an accelerator is necessarily
present in Tulchinsky such that the properties claimed would inherently
flow. Id. at 19-21. According to Appellants, “one having ordinary skill in
the epoxy resin art would believe that, in light of references such as the
Handbook of Epoxy Resins and U.S. Pat. No. 6,649,729, and contrary to the
Office’s statement, an accelerator would no doubt be necessary to afford fast
cure times.” Id. at 21.
The Examiner responds that because Tulchinsky discloses that their
bis(aminomethyl)cyclohexanes can be used as an epoxy curing agent, they
are therefore taught or suggested to be used to cure/cross-link epoxy resins
and the formulation resulting from that use is a curable formulation as
required by claim 1. Ans. 12. The Examiner additionally notes that
Appellants’ citation to US Patent No. 6,649,729 for the proposition that a
skilled artisan would have been motivated to use an accelerator in
Tulchinsky’s suggested composition “fails to establish that accelerators are
required for all amine curatives.” Id. at 13 (quoting with emphasis US
6,649,729 “Some of the curable mixtures based on epoxy resins and on said
amine compounds have long curing times.”)
Appellants do not separately argue the patentability of claims 1—5, 7,
8, and 14 over Tulchinsky. Br. 17—22. In accordance with 37 C.F.R.
§ 41.37(c)(l)(iv), claims 2—5, 7, 8, and 14 will stand or fall together with
independent claim 1.
We find that the preponderance of the evidence supports the
Examiner’s findings that Tulchinsky suggests the claimed formulation of
claim 1 in that it teaches the use of the recited
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bis(aminomethyl)cyclohexanes as a curing agent for epoxy resins, which are
the essential chemical components of the claimed formulation, therefore the
claimed properties of the formulation would necessarily be present.
Appellants do not dispute that Tulchinsky teaches the claimed
bis(aminomethyl)cyclohexanes and that Tulchinsky teaches their use as a
curing agent in epoxy resins. On the record before us, there is no evidence
that an accelerant would be required by Tulchinsky’s suggested formulation.
Appellants have not filed a Reply Brief to respond to the Examiner’s finding
that accelerators are not required for all amine curatives. In the absence of
an accelerator being indicated when using Tulchinsky’s
bis(aminomethyl)cyclohexanes as a curing agent for epoxy resins, we affirm
the stated rejection of claim 1 over Tulchinsky.
With respect to the second stated obviousness rejection of claims 9-13
over Tulchinsky in view of Marten and Cameron, the Examiner finds that
Tulchinsky is silent regarding coating a substrate with the composition of
claim 1 and curing the formulation at room temperature as required by claim
13. Ans. 7. The Examiner finds that Marten evidences that epoxy-based
systems hardened by a combination of l,3-bis(aminomethyl)cyclohexane
and 1,4-bis(aminomethyl)cyclohexane are recognized as coating
compositions that rapidly harden at low/ambient temperatures. Id. at 8
(citing Martin 2:18—39, 2:63—66, 5:49—50). The Examiner further finds that
Cameron demonstrates that low/ambient curing of epoxy resins is typically
performed at temperatures below 40°C, and particularly below 25°C. Id.
(citing Cameron 8:53—60). The Examiner finds that it would have been
obvious to coat a substrate with the formulation of Tulchinsky and cure it at
room temperature because Marten demonstrates coating such an epoxy-
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based system hardened by a combination of the claimed
bis(aminomethyl)cyclohexanes and curing at low/ambient temperatures and
such temperatures are further demonstrated by Cameron. Id. at 8. The
Examiner makes similar findings with respect to claim 9, which requires that
the curable formulation of claim 1 is applied to one or both of two substrates
that are brought into a contacting relationship. Id. at 9. The Examiner
further finds that Cameron teaches that epoxy-based coatings are suitable as
adhesives. Id. (citing Cameron, Abstr.).
Appellants do not separately argue the patentability of claims 10-12
over the combination of Tulchinsky, Marten, and Cameron. Br. 22—26. In
accordance with 37 C.F.R. § 41.37(c)(l)(iv), claims 10-12 will stand or fall
together with claim 9 from which they depend.
Appellants assert that Marten teaches away from claims 9 (and 13)
“by stating the presence of a primary aliphatic monoamine is ‘essential’ to
forming a curable composition.” Br. 23, 25. Regarding Cameron,
Appellants contend that the curing agent in Cameron’s coating, sealant, or
adhesive composition is a material containing at least two, and preferably at
least three, heterocyclic secondary amine groups which are not claimed. Id.
Appellants argue that Tulchinsky has “absolutely not[h]ing to do with
coating a substrate” and “nothing to do with adhesives and adhesive
methods.” Id. Appellants additionally argue that the recited steps in claims
9 and 13 are “more than the simple substitution of one known element for
another or the mere application of a known technique to a piece of prior art
ready for the improvement.” Id. at 24, 25 (emphasis omitted).
The Examiner responds that the primary teachings of Tulchinsky
suggest the curable epoxy formulation and that one having ordinary skill in
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the art “would have recognized that curable epoxy formulations are
commonly used in adhesive applications due to their intrinsic adhesive
characteristics” and “would have recognized that adhesive applications
involve the coating of a substrate to be adhered.” Ans. 14.
On this record, the Examiner has established by a preponderance of
the evidence that Tulchinsky suggests the curable epoxy formulation of
claim 1 and that coating and adhering substrates with curable epoxy
formulations were known uses of curable epoxy formulations as evidenced
by Marten and Cameron.
ORDER
The Examiner’s decision to reject the appealed claims is affirmed.
No time period for taking any subsequent action in connection with
this appeal may be extended under 37 C.F.R. § 1.136(a)(l)(v).
AFFIRMED
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