DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . Per amendment dated 12/16/25, claims 1, 2, 6-18, are currently pending in the application.
Claim Rejections - 35 USC § 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.
Claims 1, 2, 6, 8-18 are rejected under 35 U.S.C. 103 as being unpatentable over Lagunova (WO 2018/088919 A, cited in the IDS dated 1/10/25, of record), in view of Kim et al. (US 2019/0359755 A1).
Regarding claims 1, 2, 6, 8, 9-12, Lagunova teaches a catalyst system for polymerizing conjugated dienes, said catalyst system comprising a lanthanide compound (A), e.g., neodymium carboxylate), an alkylating agent (B), e.g., organoaluminum compound such as triethylaluminum (TEA) and diisobutylaluminum hydride (DIBAH), and a halogen-containing compound (D), e.g., organic halides and organometallic halides. Additionally, disclosed catalyst system comprises (A) a lanthanide compound, (B) an organoaluminum compound, and (D) a halogen-containing compound in a molar ratio of (A):(B):(D) at 1:(8-30):(1.5- 3.0), and use of a premixed catalyst, prepared in the presence or absence of a diene, for polymerizing conjugated dienes, such as, 1,3-butadiene, isoprene etc. (page 7, lines 19-30, page 9, lines 3-13, page 10, line 8-page 14, line 22).
Disclosed Example 8 is drawn to a catalyst system having a molar ratio of neodymium versatate:triethylaluminum:diisobutylaluminum hydride:diethylaluminum chloride at a molar ratio of 1:13.6:6:2:2.5. Thus, the molar ratio of triethylaluminum to neodymium versatate is 6:1, the molar ratio of diisobutylaluminum hydride to neodymium versatate is 2:1, and the molar ratio of halogen to lanthanum-containing compound is 2.5:1 and fall within the claimed ranges, for polymerizing butadiene in an autoclave.
Lagunova is silent on a method comprising steps as in the claimed invention.
At the outset, it is noted that in the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976). See MPEP § 2144.05.
In an analogous field, the secondary reference to Kim teaches a polydiene block copolymer using a catalyst composition comprising a lanthanide-containing compound, an organoaluminum compound and halogen sources [0055]-[0096], wherein said catalyst composition may be employed by various methods, such as by preforming the catalyst composition premixed outside the polymerization system, or alternatively, by forming it in-situ by adding the catalyst ingredients stepwise, such as by adding the alkylating agent first with the lanthanide-containing compound, and then combining the halogen source [0106]-[0109], i.e., equivalence of the methods.
Given the teaching in Kim on various methods suitable of employing the catalyst composition, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to prepare a polydiene by providing a conjugated diene monomer, introducing the Lagunova’s catalyst composition comprising the alkylating agent first with the lanthanide-containing compound, then combining the halogen source, including in amounts within the claimed molar ratios, and polymerizing the diene. That is, Lagunova’s method of catalyst addition may be substituted by Kim’s method, including with that of the claimed invention, because Kim teaches equivalence of the methods. As such, selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results; In re Gibson, 39 F.2d 975, 5 USPQ 230 (CCPA 1930), MPEP 2144.04.
With regard to claim 9, Lagunova teaches a catalyst system comprising (A) a lanthanide compound and (B) an organoaluminum compound in a molar ratio of (A):(B) at 1:(8-30), and use of trialkylaluminum, alkylaluminum hydride or a mixture thereof, i.e., equivalence of the organoaluminum compounds (page 13). Thus, given that teaching on triethylaluminum as a trialkylaluminum, it would have been obvious to a skilled artisan to include a combination of triethylaluminum and an alkylaluminum hydride in any amount within the disclosed range for the ratio. Additionally, given the teaching on equally suitable alternatives to one another, it would have would have been prima facie obvious, using no more than ordinary creativity, logic, judgment, and common sense, to combine a triethylaluminum and an alkylaluminum hydride in equal amounts (i.e., in a 1:1 molar ratio) based on the fact that both are disclosed in parallel as being equally suitable for use in this capacity, thereby obviating the claimed range. For instance, when (A):(B) is at 1:(8-20), a combination of triethylauminum and alkylaluminum hydride at a 1:1 ratio would fall within the claimed range.
Regarding claim 13, the catalyst composition of Example 1 includes 1.4 mmol Nd versatate, for polymerizing ~1028.88g butadiene (i.e., calculated by adding the amount used in the catalyst preparation). The calculated amount of Nd versatate/100g of monomer=0.136 mmol, i.e., and amount which falls within the claimed range. A skilled artisan would have found it obvious to include similar amounts in the catalyst composition comprising components as in Example 8.
Regarding claim 14, the polybutadiene of Example 8 is modified with 2-methylthiozoline to provide for modified polymer, i.e., having thiazoline functionalities.
Regarding claim 15, Lagunova teaches that the polymerizate is stopped by softened water or ethyl/isopropylalcohol, i.e., comprises a quenching step (page 20, lines 8-11).
With regard to claim 16, Lagunova teaches the 1,4-cis units in the polydienes being more than 96 wt.% (page 20, lines 15-18).
Regarding claims 17 and 18, , Lagunova teaches that the polymerization of conjugated dienes is performed until the conversion of dienes reaches 95-99% in 1.5 to 2 hours (page 19, line 27-page 20, line 1).
Claims 7 is rejected under 35 U.S.C. 103 as being unpatentable over Lagunova (WO 2018/088919 A, of record), in view of Kim et al. (US 2019/0359755 A1, Kim ‘755) and Kim et al. (US 2020/0399405 A1, Kim ‘405, of record).
The discussions on Lagunova and Kim’755, as applied to claim 1, have been incorporated herein by reference.
Lagunova is silent on method comprising a dihydride compound as claimed.
The secondary reference to Kim ‘405 is in a related field of endeavor and teaches a conjugated diene-based polymer (polybutadiene), prepared in the presence of a catalyst composition comprising a lanthanide-containing compound, a second alkylating agent, and a halide (Ab., [0010], [0038]), and a common alkylating agent, such as triethylaluminum [0081], wherein said second alkylating agent may be a dihydrocarbyl-aluminum hydride or a hydrocarbyl-aluminum dihydride. Additionally, disclosed genus of the second alkylating agents includes dihydrocarbylaluminum hydrides, such as diethylaluminum hydride, di-n-propylaluminum hydride, diisopropylaluminum hydride, di-n-butylaluminum hydride, diisobutylaluminum hydride etc., i.e., compounds within the scope of Lagunova’s orgnaoaluminum compounds, and hydrocarbylaluminum dihydrides, such as ethylaluminum dihydride, n-propylaluminum dihydride, isopropylaluminum dihydride, n-butylaluminum dihydride, isobutylaluminum dihydride etc., i.e., equivalence thereof as the second alkylating agent.
Thus, given the teaching in Kim ‘405 on a catalyst composition and components therefor, it would have been obvious to one of ordinary skill in the art, as of the effective filing date of the claimed invention, to include any of Kim’s dihydride compounds, including those of the claimed invention, in lieu of Lagunova’s monohydride compounds, based on their art recognized equivalence, absent evidence to the contrary. It is prima facie obvious to substitute equivalents known for the same purpose, so long as the equivalency is recognized in the prior art. In re Ruff, 256 F.2d 590, 118 USPQ 340 (CCPA 1958). An express suggestion to substitute one equivalent component or process for another is not necessary to render such substitution obvious. In re Fout, 675 F.2d 297, 213 USPQ 532 (CCPA 1982). See MPEP 2144.06.
Response to Arguments
In view of the amendment dated 12/16/25, the rejections of record are withdrawn, and new grounds of rejections are presented herein above. Applicant’s arguments have been duly considered. The arguments pertinent to rejections presented above are addressed herein below.
Applicant argues that Lagunova is concerned with forming the catalyst by premixing the catalyst constituents outside of the polymerization system, that Examples 8 and 9 offer similar teaching and employ the methodology of claim 1, wherein a catalyst complex is formed by mixing neodymium versatate, TIBA, and butadiene, letting this mixture age, and following aging, DIBAH and EASC are added to the mixture, that a monomer to be polymerized treated with additional DIBAH before charging the pre-formed catalyst is charged to the monomer to be polymerized.
In response, although Lagunova prescribes adding a premixed catalyst to the conjugated diene monomer for polymerization in an autoclave, the new rejections presented above rely on the secondary reference to Kim which prescribes various methods of catalyst addition, including that the claimed invention.
Applicant further presents that the polymerization of the present invention includes charging catalyst constituents directly to the polymer to be polymerized, that the neodymium compound and the alkylating agents are charged to the monomer to be polymerized, and then the polymerization is activated by the subsequent addition of the halogen-containing compound, that the procedure is consistent with examples 1-5 of the present specification which show the unexpected benefit of the present invention whereby conversion is improved where both TEAL and DIBAH are employed as the alkylating agent.
Applicant’s arguments lacks clarity. Examples 2 and 3 in TABLE 1 of the disclosure do not include DIBA/Nd catalyst but only TEAL/Nd catalyst, while Example 5 includes only DIBA/Nd catalyst. Thus, Examples 2, 3 and 5 fall outside of the scope of the claimed invention, in addition to providing for a lower conversion than Example 4 (see paragraph [00136]). While Example 4 in TABLE 1 provides for higher conversion than other Examples in TABLES 1 and 2, there is no direct comparison of the claimed method of Example 4 against the closest prior art of record to Lagunova, which teaches a catalyst composition as in the claimed invention in premixed form to be added to a diene monomer for polymerization, demonstrating unexpected results that are reasonably commensurate in scope with the claimed invention.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). Applicant is reminded of the extension of time policy as set forth in 37 CFR 1.136(a).
A shortened statutory period for reply to this final action is set to expire THREE MONTHS from the mailing date of this action. In the event a first reply is filed within TWO MONTHS of the mailing date of this final action and the advisory action is not mailed until after the end of the THREE-MONTH shortened statutory period, then the shortened statutory period will expire on the date the advisory action is mailed, and any nonprovisional extension fee (37 CFR 1.17(a)) pursuant to 37 CFR 1.136(a) will be calculated from the mailing date of the advisory action. In no event, however, will the statutory period for reply expire later than SIX MONTHS from the mailing date of this final action.
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to Satya Sastri at (571) 272 1112. The examiner can be reached Monday-Friday, 9AM-5.30PM (EST). If attempts to reach the examiner by telephone
are unsuccessful, the examiner's supervisor, Mr. Robert Jones can be reached at (571)-270-
7733. The fax phone number for the organization where this application or proceeding is
assigned is (571) 273 8300.
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/Satya B Sastri/
Primary Examiner, Art Unit 1762