Ex Parte Carlberg et al

Patent Trial and Appeal Board

Jul 18, 2016

13056194 (P.T.A.B. Jul. 18, 2016)

UNITED STA TES p A TENT AND TRADEMARK OFFICE
APPLICATION NO. FILING DATE
13/056, 194 01127/2011
132483 7590
POLSINELLI PC
c/o Blue Cube IP LLC
100 South Fourth Street
Suite 1000
St. Louis, MO 63102
07/20/2016
FIRST NAMED INVENTOR
Philip J. Carlberg
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
ATTORNEY DOCKET NO. CONFIRMATION NO.
074785-502649 1707
EXAMINER
SELLERS, ROBERT E
ART UNIT PAPER NUMBER
1765
NOTIFICATION DATE DELIVERY MODE
07/20/2016 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):
uspt@polsinelli.com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte PHILIP J. CARLBERG, HAQ. PHAM, LEMIMG
GU, ERIC B. RIPPIINGER, DAVID H. WEST, WILLIAM G.
WORLEY, and THOMAS C. YOUNG1
Appeal2015-001414
Application 13/056,194
Technology Center 1700
Before BRADLEY R. GARRIS, ADRIENE LEPIANE HANLON, and
DEBRA L. DENNETT, Administrative Patent Judges.
DENNETT, Administrative Patent Judge.
DECISION ON APPEAL 2
1 Appellants identify the real party in interest as Dow Global Technologies
LLC. App. Br. 2. We note, however, that the application was assigned to
Blue Cube IP LLC on Dec. 5, 2015, after the Appeal Brief was filed.
2 In our opinion below, we refer to the Specification filed Jan. 27, 2011
("Spec."), the Final Action mailed Mar. 10, 2014 ("Final Act."), the Appeal
Brief filed Aug. 7, 2014 ("App. Br."), and the Examiner's Answer mailed
Sept. 12, 2014 ("Ans.").
Appeal2015-001414
Application 13/056,194
STATEMENT OF CASE
Appellants appeal under 35 U.S.C. § 134 from a rejection of claims 1-
10. We have jurisdiction under 35 U.S.C. § 6(b).
We AFFIRM.
The claims are directed to an improved process for preparing a
glycidyl ether that is a solid at room temperature. Claim 1, reproduced
below, is illustrative of the claimed subject matter:
1. An improved process for preparing a glycidyl ether,
which process comprises subjecting a reaction mixture, which
reaction mixture comprises an aromatic hydroxyl-containing
compound, an epihalohydrin, water, and an inorganic hydroxide
that is at least one of alkali metal hydroxide or an alkaline earth
metal hydroxide, to conditions sufficient to produce a glycidyl
ether resin that is a solid at room temperature, the aromatic
hydroxyl-containing compound and the epihalohydrin being
present in a mole-equivalent ratio of moles (one mole-
equivalent) epihalohydrin to hydroxyl moieties of the aromatic
hydroxyl-containing compound that falls within a range of from
0.5: l tol: 1, and the epihalohydrin and alkali metal hydroxide or
alkaline earth metal hydroxide being present in a molar ratio of
the hydroxide to the epihalohydrin that falls within a range of
from 0.2:1to2:1, wherein the improvement comprises adding a
reaction solvent to the reaction mixture, the reaction solvent
being at least one alcohol ether that comprises both an ether
moiety and an alcohol moiety.
App. Br. 9 (Claim App 'x).
2
Appeal2015-001414
Application 13/056,194
Frankel
Liao et al., ("Liao")
Hwang et al.,
("Hwang")
Aritomi et al.,
("Ari to mi")
REFERENCES
us 3,313,775
us 5,028,686
us 6,001,873
JP 57-170922
Apr. 11, 1967
July 2, 1991
Dec. 14, 1999
Oct. 21, 1982
Research Disclosure Journal, Cosolventsfor making epoxy resins,
Nov. 1993 ("Cosolvents article")
REJECTIONS
The claims stand rejected as unpatentable under 35 U.S.C §103(a) as
follows:
claims 1-8 over Liao in view of Frankel;
claims 1-8 and 10 over Japanese Patent No. 57-170922 Aritomi in
view of Research Disclosure Journal (Cosolventsfor making epoxy resins)
and Liao;
claims 1-10 over Hwang in view of Research Disclosure Journal
(Cosolventsfor making epoxy resins) and Liao.
OPINION
Appellants do not present additional, separate arguments specifically
directed to the dependent claims under the rejection. Therefore, dependent
claims 2-10 will stand or fall with independent claim 1.
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Appeal2015-001414
Application 13/056,194
Rejection of claims 1--8 under 35 U.S.C. § 103(a) over Liao in view of
Frankel
Based on Liao' s disclosure that ( 1) the ratio of moles of epihalohydrin
per group reactive with an epoxide group is suitably from about 1: 1 to about
15: 1 in the reference, and (2) at ratios below about 1: 1, complete reaction of
the reactive group with the epihalohydrin cannot be achieved (Liao, col. 4,
lines 25-34 ), Appellants contend that Liao encourages a large excess of
epihalohydrin which suppresses oligomer formation and indicates that Liao
discloses the preparation of liquid epoxy resins, in contrast to the claimed
process for producing a glycidyl ether resin that is a solid at room
temperature. App. Br. 5. Appellants provide no evidence on this point, only
attorney argument. See In re Pearson, 494 F.2d 1399, 1405 (CCPA 1974)
("Attorney's argument in a brief cannot take the place of evidence.").
The Examiner finds that Liao discloses a process for preparing solid
epoxy resins. Ans. 2. Liao discloses epoxy resins having a softening point
such as 104°C (Liao, col. 10, Table I, Example 4), which would make them
solid at room temperature. Liao teaches a range of ratios of moles of
epihalohydrin per group reactive with an epoxide group from about 1: 1 to
about 15: 1 in the reference. A reference is prior art for all that it teaches,
thus one cannot ignore the lower ratio of 1: 1 disclosed by Liao. Beckman
Instruments Inc. v. LKB Produkter AB, 892 F.2d 1547, 1551 (Fed. Cir.
1989). In addition, the ratio in Liao of 1:1 overlaps the range claimed, i.e.,
from 0.5 to 1: 1. A prima facie case of obviousness typically exists when the
ranges of a claimed composition overlap the ranges disclosed in the prior art.
In re Harris, 409 F.3d 1339, 1341 (Fed. Cir. 2005). Thus, Appellants'
argument that Liao discloses a liquid epoxy resin is unavailing.
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Appeal2015-001414
Application 13/056,194
The Examiner finds that Frankel teaches preparing solid glycidyl
ethers from an aqueous slurry of a polyhydric phenol such as bisphenol A
(identified in the Specification as one of the preferred aromatic hydroxyl-
containing compounds (Spec. 6-7)) and a halohydrin such as
epichlorohydrin, wherein the molar ratio of halohydrin to polyhydric phenol
is preferably from about 0.1: 1 to 1.6: 1. Ans. 3 (citing Frankel col. 1, lines
64---67; col. 2, lines 7-20). This molar ratio overlaps the range claimed in
claim 1. App. Br. 9. The Examiner also finds that Frankel teaches a second
step wherein aqueous alkali hydroxide solution, such as sodium or potassium
hydroxide is added. Ans. 3. The Examiner quotes Frankel: "[a]s the amount
of the halohydrin is decreased, the molecular weight of the resulting resin
will increase. Id. (quoting Frankel col. 2, lines 10-20).
The Examiner states that it would have been obvious to react the
epihalohydrin of Liao with bisphenol A of Frankel in the claimed ratio in
order to maximize the molecular weight as taught by Frankel. Id.
Because Liao does not teach away from a solid epoxy resin as
Appellants contend, Appellants' argument that one of ordinary skill in the
art would not combine the teachings of Frankel with the teachings of Liao is
unpersuasive. Appellants fail to show error in the Examiner's finding that
claims 1-8 are rendered obvious by Liao in view of Frankel.
Rejection of claims 1--8and10 under 35U.S.C.§103(a) over Aritomi
in view of Cosolvents article and Liao
Appellants' argument that Aritomi in view of the Cosolvents article
and Liao centers on Appellants' position as stated above that Liao discloses
preparation only of liquid epoxy resins. App. Br. 5---6. Appellants contend
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Appeal2015-001414
Application 13/056,194
that there is therefore no suggestion or motivation to combine Liao with
Aritomi or the Cosolvents article.
The Examiner finds that Aritomi discloses a solid epoxy resin
produced from dihydric phenol (such as biaphenol A) and epichlorhydrin in
an organic solvent, then adding an aqueous solution of an alkali metal
hydroxide. Ans. 4. Epichlorhydrin is present in an amount of 0.5 to 0.8
moles per phenolic hydroxyl equivalent (Derwent abstract), which falls
within the range of 0.5: 1 to 1: 1 claimed in claim 1. The Examiner provides
calculations demonstrating that the ratios of alkali metal hydroxide to
epichlorohydrin overlap the range of ratios claimed for these compounds;
Appellants do not dispute the calculations. Furthermore, the Examiner
provides adequate reason to combine the teachings of Aritomi with solvents
taught by Liao or the Cosolvents article.
For the reasons discussed above, Appellants fail to rebut the
Examiner's prima facie case of obviousness based on this combination of
references.
Rejection of claims 1-10 under 35 U.S.C. § 103(a) over Hwang in
view of Research Disclosure Journal article and Liao
The Examiner finds that both Hwang (col. 2, lines 50-53) and Liao
(col. 4, lines 25-29) disclose reacting, in the presence of alkali metal or
alkaline earth metal hydroxides, a molar equivalent ratio of epihalohydrin to
hydroxyl group-containing aromatic compound of as low as about 1: 1 to
yield solid epoxy o-cresol novolac resins (Hwang, col. 3, Example 1, lines
22-24 and Liao, cols. 10-12, Table 1, Examples 2 and 4). Ans. 10.
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Appeal2015-001414
Application 13/056,194
The Examiner acknowledges that the claimed alcohol ether reaction
solvent is not found in Hwang. Ans. 7. However, Hwang is said to disclose
organic solvents such as secondary alcohols and C1-s alkyl ethers. Id. at 6
(citing Hwang col. 2, lines 3, 7-11, and 14--17). The Examiner finds that it
would have been obvious to use alcohol ethers disclosed in Liao (col. 8,
lines 7-11) or the Cosolvents article (page 2) (and in claim 3) as the
secondary alcohol (organic solvent) of Hwang, as Liao teaches the non-
reaction of alcohol ethers with the components of the reaction mixture, and
that they have a boiling point such that they are not totally removed during
co-distillation of water, epihalohydrin and solvent, thereby improving
Hwang's process. Ans. 10-11.
Appellants assert that both Liao and the Cosolvents article disclose
preparation of liquid epoxy resins. App. Br. 7. Based on this, Appellants
contend that there is no motivation to combine Liao with Hwang, as "[i]t is
therefore not reasonable to consider that what is suitable for a reaction where
there is an excess of epihalohydrin [Liao], thereby producing liquid epoxy
resins, would necessarily also be suitable for a reaction to produce solid
epoxy resins where there is no such epihalohydrin excess [Hwang]."
Based on this evidence before us, Appellants have not shown that the
Examiner erred in finding claims 1-10 obvious over Hwang in view of the
Cosolvents article and Liao.
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Appeal2015-001414
Application 13/056,194
DECISION
For the above reasons, the Examiner's rejection of claims 1-10 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 )(iv) (2009).
AFFIRMED
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