DETAILED ACTION
Status of Application
This action is responsive to non-provisional application filed 05/10/2024. Following entry of the preliminary amendment filed 08/16/2024, original claims 1, 3-4, 11, 13-15, and 17-19 remain pending and under examination herein.
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . However, in the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for a rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
Information Disclosure Statement(s)
The information disclosure statement(s) (IDS) filed 05/10/2024, 08/26/2024, and 07/10/2025 are in compliance with the provisions of 37 CFR 1.97, 1.98 and MPEP § 609, and therefore the information referred to therein has been considered as to the merits. Initialed copies of the IDS are included with the mailing/transmittal of this Office action.
Claim Rejections – 35 U.S.C. 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 18-19 are rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Regarding Claim 18, the recitation "greater than about 75 wt%" (see line 5) renders the claim indefinite, since the term "about" has been held to allow some flexibility [see Amgen, Inc. V. Chugai Pharmaceutical Co., 18 USPQ2d 1016, 1030 (Fed. Cir. 1991) and In re Erickson, 145 USPQ 207 (CCPA 1965)] and the specification provides no definition or standard for ascertainment of the intended degree of flexibility. Thus, the term "about" allows some tolerance below precisely 75 wt%, and it is unclear if "greater than" is intended to eliminate that tolerance. See Ex parte Lee, 31 USPQ2d 1105, 1107 (BPAI 1993). For purposes of substantive examination, the Office is construing "about 75 wt%" as readable on weight percent values less than precisely 75 wt% (e.g., 74.5 wt%), and is therefore reading claim 18 as inclusive of embodiments wherein the PIB comprises a first portion comprising polymer having alpha-vinylidene groups in a proportion equal to that of the mid-range vinylidene PIB as defined in claim 19 (wherein the corresponding "first portion" is less than 75 wt%).
Regarding Claim 19, it is noted that the same limitation of “internal vinylidene groups” is used to define both “a second portion” and “a third portion” of the PIB product effluent (see lines 4-5). The identical definition creates confusion and uncertainty as to how the “second” and “third” portions are to be differentiated for purposes of claim interpretation. For purposes of substantive examination, an assumption has been made that the first occurrence of said limitation was intended to read --beta vinylidene groups-- as in claim 18 above and consistent with the relevant description herein (cf., Spec., [0107]); however, clarification and appropriate correction are required.
Common Ownership Notice
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim Rejections – Non-statutory Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1, 3-4, 11, 13-15, and 17-19 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-3, 9, 11-13, and 15-17 of U.S. Patent No. 12,116,426 B1 (’426 patent).
Although the claims at issue are not identical, they are not patentably distinct from each other because they differ merely in matters of scope and/or semantics. Thus, pending claim 1 recites a process for forming isobutylene, the process comprising:
hydroisomerizing 1,3-butadiene present in a C4 feed to form a hydroisomerization product effluent comprising isobutylene and 2-butene; and
forming an isobutylene feed by separating the isobutylene from the hydroisomerization product effluent.
Claim 1 of ‘426 patent also is drawn to a process for forming isobutylene, the process reciting identical “hydroisomerizing” and “forming” steps to those in pending claim 1, followed by steps of: “separating the 2-butene from the hydroisomerization product effluent; isomerizing at least a portion of the 2-butene that is separated from the hydroisomerization product effluent to form an isomerization product effluent comprising normal butylenes and isobutylene; and hydroisomerizing the isomerization product effluent.” While the final two steps of the patented process are not positively recited in the pending claims, pending claim 1 is couched in open (comprising) language and therefore does not exclude a process for forming isobutylene which includes the corresponding additional steps of the patented invention.
Based on analogous reasoning, pending claim 4, drawn to a process for forming polyisobutylene, reads on claim 3 of ‘426 patent, which is drawn to a corresponding process, in view of the identity of the mutually recited “hydroisomerizing,” “separating,” “forming” and “reacting” steps, and given the open claim language.
Finally, it is noted that pending claims 11, 13-15, and 17-19 appear coextensive in scope with claims 9, 11-13, and 15-17, respectively, of ‘426 patent.
Based on the above analysis, the listed claims of ‘426 patent are considered to anticipate the scope of the pending claims. Accordingly, it would have been obvious to one of ordinary skill in the art at the time of effective filing to practice the pending claims when in possession of the patented claims. Thus, the pending claims are obvious variants of the patented claims.
Claim Rejections – 35 U.S.C. 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 3-4, 11, 13, 15 and 18-19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Chodorge et al (US 5877365) (‘Chodorge’).
Regarding Claim 1, Chodorge has already disclosed a process for forming isobutylene (see
Abstract, "process for conversion of an olefinic C4 cut to polyisobutene and to propylene by metathesis";
and col. 3, lines 13-14; "obtain an effluent containing mainly 2-butene and isobutene (the latter being
synonymous with recited "isobutylene"), the process comprising:
hydroisomerizing 1,3-butadiene present in a C4 feed to form a hydroisomerization product
effluent comprising isobutylene and 2-butene (see Example 1 (cols. 7-8) and Table 1 (col. 10), detailing
conditions for hydroisomerizing a C4 cut containing 1,3-butadiene to obtain a hydrotreated effluent comprising isobutene and wherein the 1,3-butadiene had been transformed into mainly butenes, the majority of which were 2-butene); and
forming an isobutylene feed by separating the isobutylene from hydroisomerization product
effluent (see col. 4, line 61 et seq.; "to improve the quality of the products, it may be of interest to
extract the isobutene from the effluent from the preceding step before polymerisation").
Regarding Claim 3, Chodorge further discloses wherein the C4 feed comprises greater than 3
wt% of the 1,3-butadiene based on a total wt% of the C4 feed. See, e.g., Table 1 (col. 10), describing a
stream 1 Feed C4 containing 8095 parts by weight of 1,3-butadiene with a feed Total of 20629 parts by
weight, which equates to 39 wt% of 1,3-butadiene [(8095/20629) · 100 = 39.2].
Regarding Claim 4, Chodorge discloses a process for forming polyisobutylene (see col. 1, lines 6-
7; "process for the conversion of an olefinic C4 cut to polyisobutene (synonymous with recited "polyisobutylene") and to propylene", the process comprising:
hydroisomerizing a C4 feed comprising 1,3-butadiene in a hydroisomerization reactor to form a
hydroisomerization product effluent comprising isobutylene and 2-butene (see Figs. 1, 2 and col. 3, lines
17-19 ("using a C4 hydrocarbon cut containing mainly, isobutene, n-butenes, butanes, and varying
amounts of 1,3-butadiene, supplied via a line 5") and 55-61 ("following reactions are carried out
simultaneously, in the presence of hydrogen supplied via line 6: selective hydroisomerisation of 1,3-
butadiene to a mixture of n-butenes in thermodynamic equilibrium; isomerisation of 1-butene to 2-
butene, also in thermodynamic equilibrium"));
separating the isobutylene from hydroisomerization product effluent to form a first isobutylene-
containing feed (see Fig. 2 and col. 5, lines 5-6; separation of isobutene in zone 4 from effluent of the
first step (zone 1));
forming a reaction mixture comprising a polymerization catalyst and the first isobutylene-
containing feed (see Fig. 2, col. 4, lines 54-56 ("aim of the second step (zone 2) is to polymerise the isobutene present in the C4 cut from the preceding step, for example to polyisobutene") and col. 5, lines
5-10 ("Polymerisation is carried out using a Lewis acid catalyst ..."; implicitly, such use requires forming a
reaction mixture comprising said catalyst and an isobutene feed to zone 2);
reacting the reaction mixture in a polymerization reactor, to form a polymerization product
effluent comprising polyisobutylene (PIB) (see Fig. 2 and col. 5, lines 17-22 (detailing polymerization
reaction temperature/pressure conditions) and col. 5, lines 29-30 ("separation section … where the
polymer leaving via line 8 (i.e., as product effluent) is separated")).
Regarding Claim 11, Chodorge discloses the process of claim 4 as discussed above, wherein the
C4 feed comprises the 1,3-butadiene, and one or more C4 olefins different from the 1,3-butadiene (see
Table 1 - "2 Feed hydroisomerisation" comprises 8095 parts by weight of 1,3-butadiene and plural C4
olefins different from 1,3-butadiene, namely: isobutene, 1-butene and 2-butenes).
Regarding Claim 13, Chodorge discloses the process of claim 4 as discussed above. Chodorge
further discloses wherein the C4 feed comprises a crude C4 stream that is produced from a steam
cracker used to make light hydrocarbon olefins (see Example 1 in cols. 7-8, especially col. 7, lines 56-57;
"C4 cut leaving a steam cracker had the composition shown in Table 1 (stream 1) … Firstly, the C4 cut was
hydroisomerised").
Regarding Claim 15, Chodorge discloses the process of claim 13 as discussed above. Chodorge
further discloses wherein the crude C4 stream that is produced from the steam cracker comprises 3 wt%
or more of the 1,3-butadiene based on a total wt% of the crude C4 stream (see col. 7, lines 56-57 ("C4
cut leaving a steam cracker had the composition shown in Table 1 (stream 1)") and Table 1 (col. 10),
describing a stream 1 Feed C4 containing 8095 parts by weight of 1,3-butadiene with a feed Total of
20629 parts by weight, which equates to 39 wt% of 1,3-butadiene [(8095/20629) · 100 = 39.2].
Regarding Claims 18-19, Chodorge discloses the process of claim 4 as discussed above.
Chodorge is silent as to contents of: polymer chains having alpha vinylidene groups, polymer chains
having beta vinylidene groups, and polymer chains having internal vinylidene groups in the disclosed PIB
product. However, Chodorge teaches the same process steps as claimed herein (cf., claim 4), including
an initial step of hydroisomerizing a C4 feed comprising 1,2-butadiene in a hydroisomerization reactor
under operating conditions within the scope of the present invention. See, e.g., Chodorge Example 1,
detailing hydroisomerization of a C4 cut in a first reactor at a pressure of 2 MPa (= 290 psi), an inlet
temperature of 50°C, an outlet temperature of 95°C, and over a catalyst constituted by Pd on alumina
which had been sulphurized. Similarly, operating conditions of the Applicant's hydroisomerization unit
include a temperature that may be from about 20°C to about 200°C, such as from about 50°C to about
150° C, such as from about 60°C to about 150°C; a pressure that may be from about 50 pounds per
square inch gauge (psig) to about 600 psig, such as from about 50 psig to about 500 psig, such as from
about 50 psig to about 400 psig; and a catalyst that may include a Pd metal adsorbed on a substrate, the
substrate being a metal oxide such as gamma alumina, and the Pd catalyst may be sulfurized (cf., para
[0057] of instant specification). Given the identity of process steps and hydroisomerization conditions, a
plausible basis exists to support an inference that, prima facie, the process of at least Example 1 of
Chodorge inevitably yields a PIB product comprising polymer chains having a content and type of
vinylidene groups as claimed. Where, as here, there is sound basis for believing that the products of the
Applicant and the prior art are the same, the Applicant has the burden of showing that they are not. In
re Spada, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
Claim Rejections – 35 U.S.C. 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claim 14 is rejected under 35 U.S.C. 103 as being unpatentable over Chodorge in view of Cosyns et al (US 4409410) (‘Cosyns’).
Regarding Claim 14, Chodorge discloses the process of claim 13 as discussed above. Chodorge
does not directly disclose wherein a steam cracker feed to the steam cracker comprises ethane,
butanes, hexanes, naphtha, or combinations thereof. However, Chodorge recognizes that a C4
hydrocarbon cut which contains mainly 1,3-butadiene, isobutene, n-butenes and butanes, accompanied
by traces of acetylenic hydrocarbons, is among the heavier products provided by steam cracking of feeds
constituted by light paraffin cuts (see col. 1, lines 13-18). In this regard, it is also well-known that steam
cracking of naphtha yields compositionally similar olefin cuts containing butadiene, 1-butene, 2-butenes,
and isobutene as confirmed by Cosyns (see col. 1, lines 17-35). Therefore, artisans of ordinary skill
would have reasonably expected a steam cracker feed comprising naphtha to be a viable precursor to
obtaining the desired olefinic C4 cut used in the conversion of Chodorge. Accordingly, at the time of
effective filing, it would have been obvious to one of ordinary skill in the art to modify Chodorge such
that the steam cracking cut used in the disclosed process is produced from a steam cracker wherein the steam cracker feed comprises naphtha, as claimed. The proposed modification merely involves the
straightforward selection of a known material (naphtha) to perform its previously established function
(producing olefinic C4 cut via steam cracking). Indeed, the selection of a known element/material based
on its suitability for its intended use has been held to be prima facie obvious (see MPEP § 2144.07).
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Chodorge in view of Baxter, Jr., et al (US 6884858 B2) (‘Baxter’).
Regarding Claim 17, Chodorge discloses the process of claim 4 as discussed above. Chodorge further discloses wherein the polymerization reactor comprises a tubular loop reactor (see col. 5, lines 22-25; "[w]hen the catalyst is solid, the heat of reaction can be removed by circulating the reaction mixture in a reactor loop through an external exchanger"). Chodorge does not directly disclose wherein the polymerization reactor comprises a tubular loop reactor employing a circulation loop independent of a feed flow of the first isobutylene-containing feed to the polymerization reactor; and one or more of:
a velocity of the reaction mixture in the tubular loop reactor is about 3 ft/sec (about 0.9 m/sec) or more;
a Reynolds number of the reaction mixture polymerized is about 2,000 or more;
a ratio of a circulation flow of the reaction mixture to the feed flow of the first isobutylene-containing feed is from about 10:1 to about 50:1;
the reacting the reaction mixture is performed for about 4 minutes or less; or combinations thereof.
However, in analogous art drawn to a liquid phase cationic polymerization process for producing polyolefin products comprising PIB (see col. 6, lines 40-56; col. 9, lines 63-65), Baxter teaches a preferred embodiment wherein the process is conducted in a tubular loop reactor, namely a four-pass shell-and-tube heat exchanger with a recirculation system (see Fig. 1, col. 11, lines 1-11 and col. 12, lines 3-9).
Baxter indicates that with the described recirculation system, the rate of feedstock introduction and the rate of product removal are each independent of the circulation rate (see col. 12, lines 45-48 and cf. claim 17, lines 2-4). Baxter in Example 1 discloses an embodiment wherein low molecular weight, highly reactive polyisobutylene is produced in the reactor illustrated in Fig. 1 thereof, and wherein reactor data and dimensions are set forth in Table 4 (see col. 15). The data presented in Table 4 include a combination of the four limitations recited in claim 17, line 6 et seq.; in particular:
a velocity of the reaction mixture in the tubular loop reactor of about 3 ft/sec or more (Table 4:
Linear velocity inside tubes: 9.3 ft/sec);
a Reynolds number of the reaction mixture polymerized of about 2,000 or more (id., Reynolds
number: 3180);
a ratio of a circulation flow of the reaction mixture to the feed flow of the first isobutylene-
containing feed is from about 10:1 to about 50:1 (id., Recirculation flow rate/Feedstock flow rate = 50 gpm/1.7 gpm = 29.4); and
reacting the reaction mixture is performed for about 4 minutes or less (id., Residence time: 59.6
seconds).
Baxter further teaches applicability of the disclosed process to polymerizing olefinic components that may comprise isobutylene and, alternatively, either a C3 to C15 linear alpha olefin or a C4 to C15 reactive non-alpha olefin such as 2-butene (see col. 6, lines 50-65). In light of this teaching, artisans of ordinary skill would have reasonably expected the Baxter process to be applicable to polymerizing the isobutene extract of the C4 cut treated as per Chodorge. Accordingly, at the time of effective filing, it would have been obvious to one of ordinary skill in the art to modify the process of Chodorge by utilizing as the polymerization loop reactor, a four-pass shell-and-tube heat exchanger reactor as per Baxter, motivated by an expected improvement in efficiency and economics of the polyolefin production process, consistent with the teachings of Baxter (see col. 4, line 38 et seq.).
Conclusion
Claims 1, 3-4, 11, 13-15, and 17-19 are rejected. No claims are in condition for allowance at this time.
Correspondence
Any inquiry concerning this communication should be directed to Examiner F. M. Teskin whose telephone number is (571) 272-1116. The examiner can normally be reached on Monday through Friday from 9:00 AM - 5:30 PM.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner's supervisor, Robert Jones, can be reached at (571) 270-7733. The appropriate fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/FRED M TESKIN/Primary Examiner, Art Unit 1762
/FMTeskin/08-20-26
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