Ex Parte Zhao et al

Patent Trial and Appeal Board

Sep 1, 2017

14132547 (P.T.A.B. Sep. 1, 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.
14/132,547 12/18/2013 Yiqiang Zhao 12027S-US-NP 9635
8015 7590 09/06/2017
CYTEC INDUSTRIES INC.
1937 WEST MAIN STREET
STAMFORD, CT 06902
EXAMINER
BROOKS, KREGGT
ART UNIT PAPER NUMBER
1764
NOTIFICATION DATE DELIVERY MODE
09/06/2017 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):
S tamfordPatent @ solvay.com
Cheryle. Telesco @ solvay. com
PTOL-90A (Rev. 04/07)
UNITED STATES PATENT AND TRADEMARK OFFICE
BEFORE THE PATENT TRIAL AND APPEAL BOARD
Ex parte YIQIANG ZHAO, DALIP KOHLI, and KELTOUM OUZINEB
Applicant: CYTEC INDUSTRIES INC.
Appeal 2017-001196
Application 14/132,547
Technology Center 1700
Before CATHERINE Q. TIMM, JEFFREY B. ROBERTSON, and
JANE E. INGLESE, Administrative Patent Judges.
INGLESE, Administrative Patent Judge.
DECISION ON APPEAL
Appellant requests our review under 35 U.S.C. § 134(a) of a final
rejection of claims 1—3, 5, 6, 9—11, 18, and 19.1 We have jurisdiction under
35 U.S.C. § 6(b).
We REVERSE.
STATEMENT OF THE CASE
The claimed subject matter is generally directed to, inter alia, a
discrete, corrosion-inhibiting microgel that comprises a cross-linked
polymer network created by emulsion polymerization within which organic
1 Claims 12, 13, and 15—17 stand withdrawn from consideration. Final
Office Action entered December 22, 2015 (“Final Act.”), 2.
Appeal 2017-001196
Application 14/132,547
corrosion-inhibiting compounds are entrapped or immobilized. App. Br. 2.
Claim 1 illustrates the subject matter on appeal and is reproduced below:
1. A discrete, corrosion-inhibiting microgel comprising:
a cross-linked polymer network created by emulsion
polymerization of monomers selected from: mono-functional or
bi-functional acrylic monomers; mono-functional or
bifunctional methacrylic monomers; mono-functional vinyl
monomers, and combinations thereof; and
organic corrosion-inhibiting compounds entrapped or
immobilized within the polymer network,
wherein emulsion polymerization is carried out in the
presence of an initiator for free radical polymerization and
cross-linking monomers selected from: diacrylates;
dimethacrylates; triacrylates; trimethacrylates; dipentaerythritol
pentaacrylate; pentaerythritol tetraacrylate; divinylbenzene
(DVB), derivatives of methylenebisacrylamide; and
combinations thereof, and
wherein the corrosion-inhibiting compounds are
releasable from the polymer network upon exposure to a
corrosion-triggering condition selected from: pH change,
moisture exposure, temperature increase, and combination
thereof.
App. Br. 10 (Claims App’x).
The Examiner sets forth the following rejections in the Final Office
Action, and maintains the rejections in the Answer entered August 26, 2016
(“Ans.”):
I. Claims 1—3, 18, and 19 under 35 U.S.C. § 103(a) as
unpatentable over Li et al. (US 2013/0017612 Al, published January 17,
2013 (hereinafter “Li”)) in view of Saunders et al. (US 2008/0254133 Al,
published October 16, 2008 (hereinafter “Saunders”)) as evidenced by
2
Appeal 2017-001196
Application 14/132,547
Marquez-Lucero et al. (US 5,574,377, issued November 12, 1996
(hereinafter “Marquez-Lucero”));
II. Claim 5 under 35 U.S.C. § 103(a) as unpatentable over Li in
view of Saunders as evidenced by Marquez-Lucero and Jariwala et al. (US
6,284,843 Bl, issued September 4, 2001 (hereinafter “Jariwala”)); and
III. Claims 6 and 9—11 under 35 U.S.C. § 103(a) as unpatentable
over Li in view of Saunders and Shah et al. (US 2010/0247922 Al, published
September 30, 2010) as evidenced by Marquez-Lucero.
DISCUSSION
Upon consideration of the evidence relied-upon in this appeal and the
respective positions advanced by Appellant and the Examiner, Appellant has
persuaded us that the Examiner does not carry the burden of establishing a
prima facie case of obviousness within the meaning of 35 U.S.C. § 103(a).
In re Oetiker, 977 F.2d 1443, 1445 (Fed. Cir. 1992) (“[T]he examiner bears
the initial burden ... of presenting a prima facie case of unpatentability.”);
In re Piasecki, 745 F.2d 1468, 1472 (Fed. Cir. 1984). Accordingly, we do
not sustain the Examiner’s rejections of claims 1—3, 5, 6, 9—11, 18, and 19
under 35 U.S.C. § 103(a) for the reasons set forth in the Appeal Brief and
below.
We decide this appeal based on claim 1 alone because each of claims
2, 3, 5, 6, and 9—11 depend directly or indirectly from claim 1, and claims 18
and 19 recite corrosion-inhibiting microgels and particles, respectively,
produced by emulsion polymerization as recited in claim 1.
The Examiner finds that Li discloses discrete, corrosion-inhibiting
microparticles comprising a cross-linked polymer matrix in which organic
3
Appeal 2017-001196
Application 14/132,547
corrosion-inhibiting compounds are entrapped or immobilized. Final Act. 3.
The Examiner finds that Li discloses that the particles may be formed from
polymethyl methacrylate monomers, which the Examiner finds correspond
to the mono functional methacrylic monomers recited in claim 1. Id. The
Examiner finds that Li further discloses that the microparticles may be also
be formed from pentaerythritol tetraacrylate, and the Examiner finds that
because “pentaerythritol tetraacrylate has four unsaturated ethylenic groups,
it is capable of crosslinking acrylic polymers,” and thus corresponds to a
cross-linking monomer as recited in claim 1. Final Act. 3^4.
The Examiner finds that although a particular embodiment disclosed
in Li describes forming microparticles by polycondensation, Li does not
specifically disclose how pentaerythritol tetraacrylate and monomers of
polymethyl methacrylate could be polycondensed. Ans. 14—15; Final Act. 4.
Based on this finding, the Examiner finds further that Li thus makes clear
that the microparticles of Li’s invention can be produced by polymerization
methods other than polycondensation. Id. In particular, the Examiner finds
that “the functional groups are an ester group and an ethylenic double bond,
and no insight comes from Li as to how such a group would be subject to
polycondensation.” Ans. 15. The Examiner finds that one of ordinary skill
in the art, therefore, would have looked to Saunders’ teaching that free
radical polymerization may be used to polymerize a variety of monomers,
and results in a narrow particle size that can be varied over a large range.
Ans. 14—15. The Examiner finds that in view of Saunders’ disclosure of
such advantages of free radical polymerization, and because “Li does not
provide information as to the method of polymerizing materials such as
pentaerythritol tetraacrylate and polymethyl methacrylate and/or its
4
Appeal 2017-001196
Application 14/132,547
monomers,” one of ordinary skill in the art would have been led to utilize
free radical polymerization as disclosed in Saunders to prepare
microparticles from the polymethyl methacrylate monomers and
pentaerythritol tetraacrylate disclosed in Li. Ans. 15.
However, Li explicitly indicates that the polymer backbone of the
cross-linked polymer matrix disclosed in the reference includes hydrolysable
groups, such as ester linkages. Li 1 54. Li discloses that such linkages
undergo hydrolysis when alkaline pH conditions develop at the onset of
corrosion, causing the polymers to degrade and resulting in release of
entrapped corrosion inhibitors. Id. H 7, 54. In contrast, Saunders discloses
microgel particles comprising a polymer network that expands or swells in
response to an increase or decrease in pH, rather than degrading as described
in Li. Saunders H 21, 24, 33.
Nevertheless, the Examiner finds that Saunders discloses
“methacrylates formed with multifunctional monomers having ester, thus
hydrolysable linkages,” citing paragraph 83 of Saunders. Ans. 15. The
Examiner further contends that “Li, like Saunders and the presently claimed
invention, uses particles that have hydrolysable linkages due to the presence
of polyfimctional acrylates.” Ans. 17—18.
However, paragraph 83 of Saunders indicates that monomers suitable
for free radical polymerization include substituted functional acrylates,
which are similar to the methyl methacrylate monomers disclosed in Li (1
62). Saunders 183. As Appellant points out, one of ordinary skill in the art
would have understood that free radical polymerization of such monomers
would not result in a polymer backbone having hydrolysable ester linkages,
5
Appeal 2017-001196
Application 14/132,547
but would instead result in a backbone of -C-C- groups.2 App. Br. 3—5;
Reply Br. 2—3. Due to the absence of hydrolysable backbone linkages,
Saunders’ microgel particles therefore swell, rather than degrade, when
exposed to alkaline pH. Saunders H 21, 24, 33.
Accordingly, the Examiner does not provide a sufficient factual basis
to support the finding that one of ordinary skill in the art would have formed
microparticles composed of a cross-linked polymer matrix in which
corrosion-inhibiting compounds are entrapped or immobilized as disclosed
in Li from polymethyl methacrylate monomers and pentaerythritol
tetraacrylate using free radical polymerization as disclosed in Saunders,
because doing so would result in a polymer matrix having a polymer
backbone that is not susceptible to hydrolysis in alkaline pH, and would
therefore not release the immobilized corrosion inhibitors at the outset of
corrosion. In re Schulpen, 390 F.2d 1009, 1013 (CCPA 1968) (explaining
that an obviousness rejection cannot stand when the modification proposed
by the Examiner would run counter to the teaching of a prior art reference).
Accordingly, the Examiner does not provide a sufficient factual basis
to establish a prima facie case of obviousness of the subject matter recited in
claims 1—3, 5, 6, 9—11, 18, and 19 within the meaning of 35 U.S.C. § 103(a).
We therefore do not sustain the Examiner’s rejections of these claims.
2 See, e.g., Free Radical Polymerization, Chemistry LibreTexts,
https://chem. libretexts. org/LibreT exts/Purdue/Purdue_Chem_26100%3 A_0
rganic_Chemistry_I_(Wenthold)/Chapter_08%3A_Reactions_of_Alkenes/8.
7.%09Polymerization/Free_Radical_Polymerization.
6
Appeal 2017-001196
Application 14/132,547
DECISION
In view of the reasons set forth in the Appeal Brief and above, the
Examiner’s rejections of claims 1—3, 5, 6, 9—11, 18, and 19 under 35 U.S.C.
§ 103(a) are reversed.
REVERSED
7
Notice of References Cited
Application/Control No.
14/132,547
Applicant(s)/Patent Under Patent
Appeal No.
Examiner Art Unit
1764 Page 1 of 1
U.S. PATENT DOCUMENTS
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Country Code-Number-Kind Code
Date
MM-YYYY Name Classification
A us-
B us-
C US-
D US-
E US-
F US-
G US-
H US-
1 US-
J US-
K US-
L US-
M US-
FOREIGN PATENT DOCUMENTS
* Document Number
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Date
MM-YYYY Country Name Classification
N
O
P
Q
R
S
T
NON-PATENT DOCUMENTS
* Include as applicable: Author, Title Date, Publisher, Edition or Volume, Pertinent Pages)
U Free Radical Polymerization
V
w
X
*A copy of this reference is not being furnished with this Office action. (See MPEP § 707.05(a).)
Dates in MM-YYYY format are publication dates. Classifications may be US or foreign.
U.S. Patent and Trademark Office
PTO-892 (Rev. 01-2001) Notice of References Cited Part of Paper No.
All the monomers from which addition polymers are made are alkenes or functionally substituted alkenes. The
most common and thermodynamically favored chemical transformations of alkenes are addition reactions. Many
of these addition reactions are known to proceed in a stepwise fashion by way of reactive intermediates, and
this is the mechanism followed by most polymerizations. A general diagram illustrating this assembly of linear
macromolecules, which supports the name chain growth polymers, is presented here. Since a pi-bond in the
monomer is converted to a sigma-bond in the polymer, the polymerization reaction is usually exothermic by 8 to 20
kcal/mol. Indeed, cases of explosively uncontrolled polymerizations have been reported.
Hy /
/c=^--------
H H
H □I ^ H2C = CHR
z-c-c* --------- ►
A H
RH R H III/-c-c-c-c*
III \ .
H H H H
repeat
n times
n+1
Z* is an initiating species may be a radical, a cation or an anion
It is useful to distinguish four polymerization procedures fitting this general description.
• Radical Polymerization The initiator is a radical, and the propagating site of reactivity (*) is a carbon radical.
• Cationic Polymerization The initiator is an acid, and the propagating site of reactivity (*) is a carbocation.
• Anionic Polymerization The initiator is a nucleophile, and the propagating site of reactivity (*) is a carbanion.
• Coordination Catalytic Polymerization The initiator is a transition metal complex, and the propagating site of
reactivity (*) is a terminal catalytic complex.
Radical Chain-Growth Polymerization
Virtually all of the monomers described above are subject to radical polymerization. Since this can be initiated
by traces of oxygen or other minor impurities, pure samples of these compounds are often "stabilized" by small
amounts of radical inhibitors to avoid unwanted reaction. When radical polymerization is desired, it must be started
by using a radical initiator, such as a peroxide or certain azo compounds. The formulas of some common initiators,
and equations showing the formation of radical species from these initiators are presented below.
i.s is licensee 0: NO:
Css me RRtinRidrx
(CH3)3C-01d-C(CH3)3 heat> (CH3)3C-0* + *0-C(CH3)3
ferf-butyl peroxide
O
^C6H5 0 0
0-0 —63 > C^Hg—^ * + * .^CsHg
CeHg—^ benzoyl peroxide o O
O
CM CM CM
H3C-C-M=M-C-CH3 2 H3C-C« + M2
ch3 ch3 ch3
azobisisobutyromtrile
S ssIs :ss?q ss s? is I' x- s' isc11?>u x
h3c
(CH3)3C—O" -------- *- >=0 + CH3"
llllllllllllllll .........
llllllllllillllllll|l|^llllllilllili!!lll|lil
lllllllllllllllllllllllllllllllllli^
By using small amounts of initiators, a wide variety of monomers can be polymerized. One example of this radical
polymerization is the conversion of styrene to polystyrene, shown in the following diagram. The first two equations
illustrate the initiation process, and the last two equations are examples of chain propagation. Each monomer unit
adds to the growing chain in a manner that generates the most stable radical. Since carbon radicals are stabilized
by substituents of many kinds, the preference for head-to-tail regioselectivity in most addition polymerizations is
understandable. Because radicals are tolerant of many functional groups and solvents (including water), radical
polymerizations are widely used in the chemical industry.
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Unaed States IJoense
R-O-O-R
heat
2 R-O*
R-O* + 'f!H2C=C>'
XJ
h2 ,h
C—c* ^ ideation
RO Wv
H2 ^ ./ ;y
C—C*' ^ H2C=C'
RO )=, +
H...
RO T ■-- +
Ph Ph
H2C—C/'
RO"
H
"C*
Ph Ph
H
Ph Ph Ph
a growing polystyrene chain
= Ph-
In principle, once started a radical polymerization might be expected to continue unchecked, producing a few
extremely long chain polymers. In practice, larger numbers of moderately sized chains are formed, indicating
that chain-terminating reactions must be taking place. The most common termination processes are Radical
Combination and Disproportionation. These reactions are illustrated by the following equations. The growing
polymer chains are colored blue and red, and the hydrogen atom transferred in disproportionation is colored green.
Note that in both types of termination two reactive radical sites are removed by simultaneous conversion to stable
product(s). Since the concentration of radical species in a polymerization reaction is small relative to other reactants
(e.g. monomers, solvents and terminated chains), the rate at which these radical-radical termination reactions
occurs is very small, and most growing chains achieve moderate length before termination.
Chain Termination Reactions
H R H
, , . Ill /
Polymer Chain—C-C-C-C<
III'
H H H
R
H
Combination
,R
H R H
P o I y rn e r C h a i n—C—C -C—C *
III '. .
H H H H J
HRHRRHRH
P o I y rn e r C h a i n—C -C -C -(i>'C—C -C -C - P o I v rn e r C h a i n
i i i i * i i i i
H H H H: H H H H
rs®e bend
H R H...r
;r Chain—C—C—C\C»Polymi
1 1 ' V,H H H H■t
Disproportionation
,R
<
I R H R H
-C-C-C-Poiymsr Chain
l/ 1 1 1H H H H
H R H
Polymer Chain—C-C-C=
b b H
+
R H R H
-Polymer Chain
i i i i
H H H H
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United States i.ioense
The relative importance of these terminations varies with the nature of the monomer undergoing polymerization.
For acrylonitrile and styrene combination is the major process. However, methyl methacrylate and vinyl acetate are
terminated chiefly by disproportionation.
Another reaction that diverts radical chain-growth polymerizations from producing linear macromolecules is called
chain transfer. As the name implies, this reaction moves a carbon radical from one location to another by an
intermolecular or intramolecular hydrogen atom transfer (colored green). These possibilities are demonstrated by
the following equations
Polymer
H R H R H R
I I I I I t!R—c—c—c—c—c—c*-
................. ......
H H H H H H
Chain Transfer Reactions
Intermolecular
Hydrogen Transfer
Polymer Chain
H R H R
-H-H
H H H H
-Polymer Chain
H R H R H R
I I I I I I
Polymer Cham—C-C-C—C-C-C-m
i i i i i I
H H H H H H
Polymer Chain
HR R
H H H H
-Polymer Chain
H R H2
Polymer Chsin-CfC^CHR
H hO CH2*ri H
R
Intramolecular
Hydrogen Transfer
H R H R H R
I I I I I I
P o i y m e r C h a i n—C -C -C -C -C -C -Hi • i i i I
H H H H H
Chain transfer reactions are especially prevalent in the high pressure radical polymerization of ethylene, which is the
method used to make LDPE (low density polyethylene). The 1 “-radical at the end of a growing chain is converted to
a more stable 2°-radical by hydrogen atom transfer. Further polymerization at the new radical site generates a side
chain radical, and this may in turn lead to creation of other side chains by chain transfer reactions. As a result, the
morphology of LDPE is an amorphous network of highly branched macromolecules.
Contributors
• William Reusch, Professor Emeritus (Michigan State U.), Virtual Textbook of Organic Chemistry
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