Ex Parte Keller et al

Board of Patent Appeals and Interferences

Jun 27, 2007

10808264 (B.P.A.I. Jun. 27, 2007)

The opinion in support of the decision being entered today is not
binding precedent of the Board.

UNITED STATES PATENT AND TRADEMARK OFFICE
____________

BEFORE THE BOARD OF PATENT APPEALS
AND INTERFERENCES
____________

Ex parte TEDDY M. KELLER, and DAWN D. DOMINGUEZ

____________

Appeal 2007-0650
Application 10/808,264
Technology Center 1700
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Decided: June 27, 2007
____________

Before BRADLEY R. GARRIS, CHARLES F. WARREN, and
CATHERINE Q. TIMM, Administrative Patent Judges.

TIMM, Administrative Patent Judge.

DECISION ON APPEAL
Appellants appeal under 35 U.S.C. § 134(a) from the
Examiner’s decision rejecting claims 1, 2, 22, 23, 26, 27, 56, and 58. 1
We have jurisdiction under 35 U.S.C. § 6(b). We affirm-in-part.

1 Claims 3-7, 24, 25, 28-31, and 57 are pending, but are not rejected
by the Examiner.
Appeal 2007-0650
Application 10/808,264

I. BACKGROUND
The invention relates to a polyaromatic ether, a process of
preparing the polyaromatic ether, and a process of preparing an
oligomer based on the polyaromatic ether. Claims 1, 22, and 26 are
illustrative of the subject matter on appeal:
1. A polyaromatic ether comprising the formula:

–(–O–Ar–)n– ;

wherein Ar is an independently selected divalent aromatic
radical with or without substituents containing one or
more fused aromatic rings, one more non-fused aromatic
rings without intervening functional groups, or
combinations thereof wherein the radical sites are on the
same or different aromatic rings; and

wherein n is an integer greater than or equal to 7.

22. A process of preparing a polyaromatic ether comprising the
formula:
–(–O–Ar–)n– ;

wherein Ar is an independently selected divalent aromatic
radical with or without substituents containing one or
more fused aromatic rings, one or more non-fused
aromatic rings without intervening functional groups, or
combinations thereof wherein the radical sites are on the
same or different aromatic rings;

comprising the step of reacting a dihydroxyaromatic with a
dihaloaromatic;

wherein neither the dihydroxyaromatic nor the
dihaloaromatic is present in an excess amount; and

wherein the reaction is performed in the presence of a
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copper compound and a base.

26. A process of preparing an aromatic ether oligomer
comprising the formula:

T–Ar-(–O–Ar–)n–T ;

wherein Ar is an independently selected divalent
aromatic radical with or without substituents
containing one or more fused aromatic rings, one
or more non-fused aromatic rings without
intervening functional groups, or combinations
thereof wherein the radical sites are on the same or
different aromatic rings;

wherein T is terminating group independently selected
from the group consisting of –OH and –X;

wherein X is independently selected from the group
consisting of Br and I;

wherein n is an integer greater than or equal to 1;

comprising the step of reacting a dihydroxyaromatic with a
dihaloaromatic;

wherein the reaction is performed in the presence of a
copper compound and a base; and

wherein either the dihydroxyaromatic or the
dihaloaromatic is present in an excess amount.

The Examiner relies on the following prior art references as
evidence of unpatentability:
Keller US 4,259,471 Mar. 31,1981
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Matzner US 4,968,758 Nov. 6, 1990
Matzner US 5,084,530 Jan. 28, 1992

Appellants rely on the following evidence in rebuttal:
Williams et al., “Solvent assisted Ullmann Ether Synthesis. Reaction
of Dihydric Phenols” J. Org. Chem., 32, 2501 (1967) cited in Keller
reference.

Hammann et al., “Synthesis of Seven New Polyphenyl Ethers” J.
Chem. and Eng. Data, 15(2), 352 (1970), cited in Keller reference.

Declaration under 37 CFR 1.132 of Teddy M. Keller.

The rejections as presented by the Examiner are as follows:
1. Claims 1 and 2 are rejected under 35 U.S.C. § 102(b) as
anticipated by Keller; and
2. Claims 22, 23, 26, 27, 56, and 58 are rejected under 35 U.S.C. §
103(a) as unpatentable over Matzner (4,968,758 or 5,084,530).

II. DISCUSSION
A. Anticipation by Keller
In rejecting claims 1 and 2 as anticipated by Keller, the
Examiner finds that the Keller reference describes resins with –(Oφ)x–
repeating units (x=1-10; φ=phenyl group) that are polyaromatic ethers
within the scope of claims 1 and 2 when x = 7, 8, 9, or 10 (Answer 3).
Appellants acknowledge that the Keller structures are within the scope
of the claims when x = 7, 8, 9, or 10 (Br. 3-4). Appellants contend,
however, that Keller “is not enabling for all disclosed values of x,
including 7, 8, 9, and 10” (Br. 3). Specifically, Appellants contend
that Keller fails to enable the synthesis of these polyaromatic ethers
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(Br. 3). Appellants also contend that the Ullman ether synthesis
referred to by Keller, in declarant Keller’s expert opinion, cannot be
used to make oligomeric or polymeric aryl ethers in high yield and
high molecular weight (Br. 3 referring to the Keller Declaration).
Based on the contentions advanced in the Briefs and Answer
the issue is: Have Appellants presented sufficient evidence to show
that one of ordinary skill in the art would not be able to synthesize the
polyaromatic ethers with values of x of 7, 8, 9, or 10 taught by Keller
at the time of the invention?
We select claim 1 as representative in deciding the above issue.
It is well settled that prior art under 35 U.S.C. § 102(b) must be
“enabling”, i.e., it “must sufficiently describe the claimed invention to
have placed the public in possession of it.” In re Donohue, 766 F.2d
531, 533, 226 USPQ 619, 621 (Fed. Cir. 1985). “Such possession is
effected if one of ordinary skill in the art could have combined the
publication's description of the invention with his own knowledge to
make the claimed invention.” Id. A reference is presumed to be
enabling and therefore, once the examiner establishes that the
reference teaches each and every limitation of the claimed invention,
the burden shifts to the applicants to prove the reference is not
enabling. Chester v. Miller, 906 F.2d 1574, 1578, 15 USPQ2d 1333,
1337 (Fed. Cir. 1990); In re Sasse, 629 F.2d 675, 681, 207 USPQ 107,
111 (CCPA 1980).
As acknowledged by Appellants, Keller describes resins and
oligomers containing polyaromatic ethers within the scope of claim 1
(Br. 3-4). The burden, therefore, is on Appellants to show non-
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enablement. Keller includes the following guidance on how to
synthesize the resins:
The resins of the present invention are obtained by
heating a bisorthodinitrile of the general formula:

wherein x is an integer from 1 to 10 and the phenyl
groups are attached at the meta or para position. The
bisorthodinitriles are prepared by a nucleophilic
substitution of the nitrosubstituent of 4-nitrophthalonitrile
with an aromatic diol. The aromatic diols are easily
prepared by an Ullman ether synthesis. Further
discussion of this type of synthesis can be found in
Williams, A. L. et al. Solvent-Assisted Ullman Ether
Synthesis. Reactions of Dihydric Phenols. In Journal of
Organic Chemistry 32: p. 2501-05. August 1967 and in
Hammann, W. C. et al. Synthesis of Seven New
Polyphenyl Ethers. In Journal of Chem. and Eng. Data
15(2): p. 352-5. 1970.

(Keller, col. 3, l. 56 to col. 4, l. 8).
As shown above, Keller refers to Ullman ether synthesis
generally as useful for synthesizing the aromatic diols. These diols
are used to form the oligomers and resins containing the polyaromatic
ethers. Keller further cites two references as discussing this type of
synthesis, Williams and Hammann. In arguing that Keller does not
enable the synthesis, Appellants argue that neither Keller nor
Williams nor Hammann discloses synthesis of aromatic diols where x
is 7 or above (Br. 3).
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We cannot say that Appellants have provided sufficient
evidence and/or reasoning to support a determination that those of
ordinary skill in the art would not have been able to synthesize the
x = 7, 8, 9, or 10 aromatic diols of Keller. Looking at the issue
through the facts of the cases that have construed “possession” in the
context of what is enabling, we note that prior art references were
found to be non-enabled when there was a complete absence of a
known or obvious method of making the product in a stable form. See
In re Brown, 329 F.2d 1006, 1011, 141 USPQ 245, 249 (CCPA 1964)
(“[W]e do not think that Clark's reference to his unsuccessful attempts
to prepare fluorine-containing silicone homopolymers would place
such homopolymers in the possession of the public” (emphasis
added)); In re Sheppard, 339 F.2d 238, 241-42, 144 USPQ 42, 45
(CCPA 1964) (“Emelus indicates a complete lack of success in
preparation of pentafluorides” in a stable form (emphasis added)); In
re Hoeksema, 399 F.2d 269, 274, 158 USPQ 596, 601 (CCPA 1968)
(“[T]he absence of a known or obvious process for making the
claimed compounds overcomes a presumption that the compounds are
obvious.” (emphasis added)); In re Collins, 462 F.2d 538, 542-43, 174
USPQ 333, 337 (CCPA 1972) (“[T]he lack of a teaching in Collins of
how to make the presently claimed heat exchangers vitiates the
rejection unless there was some known or obvious way to make
them.” (emphasis added)).
Appellants present no convincing evidence that those of
ordinary skill in the art at the time of the invention would be unable to
make the diols at issue. Keller states that the aromatic diols “are
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easily prepared by an Ullman ether synthesis” (Keller, col. 3, l. 68 to
col. 4, l. 1), and this provides evidence that those of ordinary skill in
the art would have understood how to adapt an Ullman ether synthesis
method to obtain the desired diols. Keller states that Williams and
Hammann “discuss” Ullman ether synthesis. This language provided
evidence that this “discussion” would have provided enough guidance
to the skilled artisan to allow synthesis of all of the diols of Keller.
That Keller, Williams, and Hammann do not expressly disclose
forming x=7 or above diols, does not show that one of ordinary skill
in the art would not understand how to adapt the Ullman ether
synthesis method to form the higher repeating unit diols. An express
articulation of such knowledge in the references is not required where
it is evident that those of ordinary skill in the art possessed the
knowledge. See Motorola, Inc. v. Interdigital Tech. Corp., 121 F.3d
1461, 1472, 43 USPQ2d 1481, 1489 (Fed. Cir. 1997) and cases cited
therein. Moreover, it is not necessary “that an invention disclosed in a
publication shall have actually been made in order to satisfy the
enablement requirement.” In re Donohue, 766 F.2d 531, 533, 226
USPQ 619, 621 (Fed. Cir. 1985).
Appellants also rely upon the Keller Declaration in support of
their contention of non-enablement (Br. 3-4). According to the
Declaration, “[t]he Ullmann ether synthesis referred to in the Keller
reference (US Patent No. 4,259,471) cannot be used to make
oligomeric or polymeric aryl ethers in high yield and high molecular
weight.” (Declaration ¶ 3 (emphasis added)). Enablement does not
require synthesis in high yield, only the ability to synthesize.
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Moreover, what declarant Keller means by “high molecular weight” is
not clear. The evidence does not convince us that those of ordinary
skill in this art would not have known how to synthesize the x=7-10
aromatic diols of the Keller reference.
Appellants have not satisfied their burden of showing that the
Keller reference is not enabling with respect to the subject matter of
claim 1.
With respect to claim 2, Appellants note that this claim limits
the –(–O–Ar–)n– repeating unit of claim 1 to those where the Ar
groups are m- or p-phenylene and contend that these compounds are
not enabled by the Keller reference (Br. 4). However, Appellants only
argue that, in Hammann, the longest chain having only phenylene
groups has x=3. Again, the fact there is no express disclosure of
longer repeating units does not suffice to overcome the presumption
that Keller is an enabled reference for all the compounds disclosed
therein.
We sustain the rejection of claims 1 and 2 under 35 U.S.C. §
102(b) as anticipated by Keller.
B. Obviousness over Matzner
The Examiner rejects claims 22, 23, 26, 27, 56, and 58 as
obvious over two related Matzner references.2 These references are
directed to block copolymers containing poly (aryl ether) blocks and
poly(aryl ether ketone) blocks (see, e.g., Matzner ‘758, col. 4, ll. 8-
16).

2 The US 5,084,530 reference is a divisional of US 4,968,758, and the
two references have substantially the same disclosures.
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Application 10/808,264

Appellants contend that the compounds of Matzner contain
carbonyl groups between aromatic groups and such is excluded from
the scope of the claims (Br. 5). Appellants further contend that the
processes of Matzner produce only polymers containing carbonyl
groups in the main chain, no other processes involving a base and a
copper compound are disclosed (Br. 5). The Examiner contends that
the claims do not exclude the carbonyl groups of Matzner (Answer 5).
The issues are: (1) Are the claims open to the presence of the
carbonyl groups disclosed by Matzner? and (2) Has the Examiner
provided sufficient evidence showing that Matzner describes a process
involving a base and a copper compound for making the claimed
compounds?
The resolution of the first question requires a determination of
the scope of the claims. During examination “claims . . . are to be
given their broadest reasonable interpretation consistent with the
specification, and . . . claim language should be read in light of the
specification as it would be interpreted by one of ordinary skill in the
art.” In re Am. Acad. of Sci. Tech. Ctr., 367 F.3d 1359, 1364, 70
USPQ2d 1827, 1830 (Fed. Cir. 2004).
Looking at claim 22 as representative, we note that this claim is
directed to a process of preparing a polyaromatic ether comprising the
formula –(–O–Ar–)n–.
With regard to the identity of the “Ar” group, we read the claim
clause in concert with the Specification (e.g., Specification ¶¶ 20-21).
In this formula “Ar” is an independently selected divalent aromatic
radical. The radical can be any divalent radical with or without
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substituents containing one or more fused aromatic rings.
Alternatively, the radical can be “one or more non-fused aromatic
rings without intervening functional groups.” The only other option
for the “Ar” group is a combination of the two alternatives recited
above. Therefore, where “Ar” includes fused rings, there can be
substituents on the radical. Where “Ar” includes two or more non-
fused rings, there can be no functional groups between the rings.
Where “Ar” is one non-fused ring, the language “no function groups
between the rings” cannot apply.
Importantly, “n” is not limited by the claim. We, therefore,
interpret the claim as allowing n=1. The claim only requires the
presence of one –(–O–Ar–)– structure.
We also note the use of the transitional phrase “comprising.”
The use of “comprising” means that the claim is open to the inclusion
of other structures in addition to the recited –(–O–Ar–)n– structure.
Based on the above analysis of the claims, we determine that
claim 22 encompasses a process of making a polyaromatic ether with
one –(–O–Ar–)– structural group where “Ar” is a single aromatic ring.
We also determine that because the claim uses the transitional phrase
“comprising,” the claim does not exclude carbonyl groups in other
portions of the structure.
Matzner describes polyaromatic ethers meeting the
requirements of claim 22. See, for instance, formula (28) in columns
17 and 18 of Matzner. Formula (28) illustrates a block copolymer
containing –(–O–Ar–)– structural groups wherein “Ar” is a single
aromatic ring, i.e., a phenyl group. While other sections of the
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formula (28) compound include carbonyl groups, those are not
excluded by the claim.
With respect to the issue of whether the Examiner has shown
that Matzner suggests a process of preparing the compounds of the
claims, we determine that such a suggestion is present with regard to
claim 22 (e.g., Matzner ‘758, col. 18, ll. 1-13; col. 23, ll. 53-55), but
the Examiner’s findings fall short with regard to the aromatic ether
oligomer of claim 26.
The Examiner points out that Matzner describes an aromatic
ether oligomer formula starting at column 5, line 20 that encompasses
the oligomers of claim 26. The Examiner further finds that Matzner
discloses the process of preparing “said polyaromatic ether” citing
various portions of the references directed to the preparation of the
block copolymer (Answer 4). The Examiner has not cited any portion
of the reference directed to making the compounds of column 5, line
20. The Examiner, therefore, has not presented sufficient evidence
that Matzner suggests a process of reacting a dihydroxyaromatic with
a dihaloaromatic in the presence of a copper compound and a base to
prepare the oligomer in accordance with claim 26.
With respect to claims 23 and 27, Appellants point out that
these claims limit the copper compound to CuI or CuBr, compounds
not disclosed in the Matzner references (Br. 5). We consider the
Appellants’ contention with respect to claim 23 only as claim 27 is
dependent on claim 26, and, therefore, the rejection of claim 27 fails
for the reasons given with respect to claim 26.
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Matzner’s disclosure with regard to the identity of the copper
compounds is as follows:
All of the reactions discussed above may be
advantageously performed in the presence of small
amounts of cupric or cuprous ions. A wide range of
copper compounds may be used, both cupric and cuprous
compounds being usable in accordance with the present
invention. The copper compounds used should be stable
under the polymerization conditions and it is preferred
that the copper compounds be essentially anhydrous.
Copper compounds which can be used include cuprous
chloride, cupric chloride, cupric acetylacetonate, cuprous
acetate, cupric hydroxide, cuprous oxide, cupric oxide,
basic cupric carbonate and basic cupric chloride.

(Matzner ‘758, col. 23, ll. 53-64).
The disclosure that a wide range of copper compounds can be
used coupled with Matzner’s examples of the related halogenated
copper, cuprous chloride (CuCl), would have suggested the use of
other halogenated coppers including CuI and CuBr to one of ordinary
skill in the art particularly since there are only four useful members of
the halogen genus.
We sustain the rejection of claims 22, 23, and 56 under 35
U.S.C. § 103(a) as obvious over the Matzner references. We,
however, do not sustain the rejection of claims 26, 27, and 58 on those
grounds.
III. DECISION
We sustain the rejection of claims 1 and 2 as anticipated by
Keller. We sustain the rejection of claims 22, 23, and 56 as obvious
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over the Matzner references. We do not sustain the rejection of
claims 26, 27, and 58 over the Matzner references.
Accordingly, the Examiner’s decision is AFFIRMED-IN-
PART.
IV. TIME PERIOD FOR RESPONSE
No time period for taking any subsequent action in connection
with this appeal maybe extended under 37 C.F.R. § 1.136(a)(1)(iv).

AFFIRMED-IN-PART

tlc/ls

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