DETAILED ACTION
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 .
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-11 and 16-17 are rejected under 35 U.S.C. 103 as being unpatentable over Wakefield (US Patent No. 3,632,563). Odian (Principles of Polymerization Fourth Edition, Chapter 1 - Introduction) and Stavely (Industrial and Engineering Chemistry 1956, 48, 4, pp. 673-686) are cited as evidentiary references.
Regarding claim 1, Wakefield teaches synthetic polyisoprenes (Abstract), and teaches a group of commercially satisfactory inventive polymers having between about 80 and 96% cis-1,4-structures, about 0 to about 10% trans-1,4-structures, and about 3 to about 10% 3,4-structures (col. 3, lines 31-38). The percentage of 3,4-structures overlaps the claimed range of “at least 10%,” establishing a prima facie case of obviousness. Furthermore, the content of all 1,4 isoprene repeat units which are in the cis-configuration ranges from about 88.9% (a polymer containing a maximum amount of trans-content at 10%, and a minimum amount of cis-content at 80%, which therefore also contains 10% of 3,4-structures; the cis--content with respect to all 1,4-structures is 80% cis- / 90% total 1,4 structures, which equals about 88.9%) to about 100% (a polymer containing 0% trans-content will have 100% cis--content with respect to all 1,4-structures, regardless of the total amount of 3,4-structures). The range of about 88.9% to about 100% of cis-1,4 structures with respect to all 1,4-structures overlaps the claimed range of “wherein at least 96% of all 1,4 isoprene repeat units of the synthetic polyisoprene are cis 1,4 isoprene units,” establishing a prima facie case of obviousness
As described above, the polymer of Wakefield contains between about 0 to about 10% trans-1,4-structures (col. 3, lines 31-38), which reads on the claimed limitation requiring “substantially zero” trans 1,4 isoprene units.
Regarding claims 2-3, Wakefield is silent with regard to the claimed glass transition temperatures. Wakefield as applied above results in a polymer that is structurally identical to the claimed polymer, which contains the same structural composition. Products of identical chemical compositions cannot have mutually exclusive properties. Where the claimed and prior art products are identical or substantially identical in structure or composition, a prima facie case of obviousness has been established. See MPEP 2112.01. The claimed glass transition temperature characteristics will therefore necessarily be present in Wakefield as applied to claim 1, above.
Regarding claims 4 and 5, Wakefield teaches that the inventive polymers have weight average molecular weights ranging from 10,000 to 2,000,000 g/mol (recognized as weight-average molecular weights because they are derived from inherent viscosities, col. 6, lines 15-28).
While Wakefield does not explicitly disclose the number-average molecular weights of the inventive polymers, the number-average molecular weights as-claimed will inherently be present in the polymers of Wakefield; since weight-average molecular weight (Mw) is greater than or equal to number average molecular weight (Mn) (c.f. Odian p. 22), a range of 100,000 to 2,000,000 g/mol Mw within the teachings of Wakefield will provide the claimed Mn ranges for both claims. Furthermore, the above range would provide the claimed number-average molecular weight range (i.e., greater than or equal to 100,000 g/mol Mn) for polymers having dispersities (Đ) within the range of 1 to 20, aligned with and in excess of reasonable values for successful polymerization.
Furthermore, the polymerization of isoprene under substantially identical conditions have been shown to produce polyisoprenes having number average molecular weights within the claimed range (c.f. Stavely p. 677, Number average molecular weights of lithium-catalyzed polyisoprenes are shown within the range of 178,000 and 669,000 g/mol).
Regarding claim 6, Wakefield is silent with regard to the claimed numbers of repeat units. However, as described above, the polyisoprene of Wakefield possesses the same structural composition (i.e., the same proportion of cis--1,4 and 3,4 structural units) and possesses the same molecular weight as claimed. The claimed numbers of repeat units will therefore necessarily be present in the polymers of Wakefield; given that the molecular weight of isoprene is 68.12 g/mol, a range of about 1468 to about 11,744 repeat units will be present in both the claimed and prior art polymers, with the prior art polymers potentially containing even more repeat units.
Regarding claim 7, as described above, Wakefield contains having between about 80 and 96% cis-1,4-structures, about 0 to about 10% trans-1,4-structures, and about 3 to about 10% 3,4-structures (col. 3, lines 31-38). The polymer of Wakefield therefore contains between about 80 and about 100% of 1,4 isoprene and about 3 to about 10% of 3,4 isoprene, by weight, which overlaps the claimed characteristics, establishing prima facie cases of obviousness.
Regarding claim 8, as described above, Wakefield contains having between about 80 and 96% cis-1,4-structures, about 0 to about 10% trans-1,4-structures, and about 3 to about 10% 3,4-structures (col. 3, lines 31-38). The polymer of Wakefield therefore contains between about 80 and about 100% of 1,4 isoprene and about 3 to about 10% of 3,4 isoprene, by weight, which reads on the claimed limitation of “predominantly 1,4 isoprene.”
Regarding claims 9 and 10, as described above, Wakefield contains having between about 80 and 96% cis-1,4-structures, about 0 to about 10% trans-1,4-structures, and about 3 to about 10% 3,4-structures (col. 3, lines 31-38). The content of all 1,4 isoprene repeat units which are in the cis-configuration therefore ranges from about 88.9% (a polymer containing a maximum amount of trans-content at 10%, and a minimum amount of cis-content at 80%, which therefore also contains 10% of 3,4-structures; the cis--content with respect to all 1,4-structures is 80% cis- / 90% total 1,4 structures, which equals about 88.9%) to about 100% (a polymer containing 0% trans-content will have 100% cis--content with respect to all 1,4-structures, regardless of the total amount of 3,4-structures), which overlaps the claimed ranges of “at least 99.1%” and “at least 99.9%,” establishing a prima facie case of obviousness.
Regarding claims 16-17, the claims are recognized as product-by-process claims. Product-by-process claims are not limited to the manipulations of the recited steps, but only to the structure implied by the steps (See MPEP 2113.I.). In this case, the structure implied by the recited steps includes a polyisoprene meeting the structural limitations of claim 1 and claim 17. As described above, Wakefield teaches a polyisoprene meeting these structural limitations. The teachings of Wakefield therefore also read on the polyisoprenes of claims 16 and 17.
Claims 11 is rejected under 35 U.S.C. 103 as being unpatentable over Wakefield (US Patent No. 3,632,563) in view of Stavely (Industrial and Engineering Chemistry 1956, 48, 4, pp. 673-686).
Regarding claim 11, Wakefield teaches all of the limitations of claim 1, as described above. Wakefield teaches weight average molecular weights ranging from 10,000 to 2,000,000 g/mol (recognized as weight-average molecular weights because they are derived from inherent viscosities, col. 6, lines 15-28), but differs from claim 11 because it is silent with regard to the claimed ratio of weight average to number average molecular weight.
In the same field of endeavor, Stavely teaches the polymerization of Isoprene using lithium metal, and teaches number average molecular weights including 178,000, 230,000, and 669,000 (p. 677, Table II). Products of identical chemical compositions cannot have mutually exclusive properties. Where the claimed and prior art products are identical or substantially identical in structure or composition, a prima facie case of obviousness has been established. See MPEP 2112.01. In this case, the teachings of Stavely and Wakefield disclose polyisoprenes produced by substantially identical processes. Furthermore, the Stavely and Wakefield documents were produced by the same persons (c.f. the Authors of Wakefield and the Coworkers* section at the bottom of p. 673 of Stavely – where Wakefield and Foster are both included). The molecular weight and molecular weight distribution characteristics of both of these two documents are prima facie identical to one-another. The polymers of these two documents therefore possess weight average molecular weights ranging from 10,000 to 2,000,000 and number average molecular weights including 178,000, 230,000, and 669,000. The dispersities (Đ) of these polymers therefore range from 1 (because Mw ≥ Mn) to about 11, which encompasses the claimed range of “2 to 5,” establishing a prima facie case of obviousness.
Claims 12-20 are rejected under 35 U.S.C. 103 as being unpatentable over Wakefield (US Patent No. 3,632,563) in view of Shiba (US 2019/0256628 A1) and Meng ’16 (RSC Advances 2016, 6, 19351-19356).
Regarding claims 12-14, Wakefield exemplifies the process for polymerization of isoprene wherein a purified isoprene is provided and polymerized by contacting it with a catalyst (e.g., col. 19, Example 1, lines 1-27). Wakefield differs from claim 12 because it is silent with regard to the claimed catalyst structure, and because it is silent with regard to the activation of said catalyst. Wakefield does however make obvious a polyisoprene having the claimed compositional characteristics, as described above.
In the same field of endeavor, Shiba teaches a method for producing a conjugated diene polymer having a high content of cis-1,4 structures (abstract), comprising a ternary catalyst system including a gadolinium catalyst ((A), Abstract), an ionic compound which may be inter alia borate salt complexes such as ammonium tetrakis (pentafluorophenyl)borate ((B), [0068]-[0069]), and an organic metal compound, which may be an organic aluminum compound, and which may be a trialkyl aluminum such as triisobutyl aluminum ((C), [0081]). Shiba teaches that the inventive polymer may comprise a conjugated diene such as isoprene ([0099]), and may also comprise a copolymer of said conjugated dienes in addition to other monomers, such as norbornene ([0101]). It is prima facie obvious to substitute equivalents known in the art as suitable for the same purpose. Therefore, it would have been obvious to one of ordinary skill in the art at the time of filing to substitute the ternary catalyst system of Shiba into the formulation of Wakefield, as Shiba recognizes said system as capable of affecting the polymerization of isoprene.
As described above, Shiba teaches that the catalyst (A) is a gadolinium catalyst (Abstract), which differs from the catalyst system required by claim 12. In the same field of endeavor, Meng ‘16 teaches a copolymer of Isoprene and norbornene (Abstract), which is produced using a catalyst system containing a bis(phenoxy-imine) titanium complex (Abstract). Meng ‘16 further teaches the use of triisobutyl aluminum within the catalyst system (Abstract), and refers to prior publications indicating that ternary systems comprising a catalyst complex/alkyl aluminum/borate salt complex are useful for the polymerization of norbornene and isoprene (p. 19351, Introduction section, right column). Furthermore, as described above, Shiba contemplates that the inventive ternary catalyst system is capable of affecting the polymerization of both isoprene alone and isoprene copolymers (c.f. [0099] and [0101]). It is prima facie obvious to substitute equivalents known in the art as suitable for the same purpose (see MPEP 2144.06). Therefore, it would have been obvious to one having ordinary skill in the art at the time of filing to substitute the bis(phenoxy-imine) titanium catalyst of Meng ‘16 in place of the gadolinium catalyst within the formulation of Shiba, as Meng ‘16 teaches said titanium catalyst as a suitable catalyst for the polymerization of norbornene and isoprene. In doing so, the polymerization process of Wakefield would include the claimed catalyst system and process of polymerization for the following reasons:
i) The titanium catalyst taught by Meng ‘16 reads on the catalyst required by the polymerization method claim (claim 13), because it is identical to the claimed catalyst when:
The structure falls within the scope of claimed formula (Ia)
M is titanium
X is a halogenide (chloride)
LA and LB are identical to one-another and fall within the scope of claimed formula (II), and wherein, in claimed formula (II),
m is 2
n is 0
R groups are chosen from hydrogen (in the meta-positions, with respect to the oxygen substituent, on the benzene ring directly attached to oxygen and all other positions with respect to the nitrogen substituent on the benzene ring directly attached to nitrogen) and t-butyl groups (in the ortho-position which is not a imine-bearing substituent, and the para-position, with respect to the oxygen substituent on the benzene ring directly attached to oxygen)
This catalyst is recognized as the same catalyst described by claimed formula (IIIa) in claim 14, wherein M is titanium, each X is a chlorine atom, R1-2, R4, and R7 are all hydrogen atoms and R3, R5, R6, and R8 are all t-butyl groups.
ii) , Shiba teaches the mixing of the borate compound (component (C) of Shiba) with the catalyst (component (A) of Shiba, which is the bis(phenoxy-imine) catalyst of Shiba in view of Meng ‘16, as described above) ([0094]). This reads on the claimed method step “(C) activating the catalyst to obtain an activated catalyst” because the instant Specification states that activating the catalyst entails mixing said catalyst with an activator ([0021]), and indicates that ammonium tetrakis (pentafluorophenyl)borate is a suitable activator ([0021]; also c.f. claim 14). Shiba finally teaches the polymerization of the monomers (e.g., [0100] and [0102]).
Regarding claim 15, Shiba further teaches that the mixing of the catalytic components (A) and (C) with an inert solvent (described as aging these components, which explicitly involves their mixing, see [0091]) may be performed at temperatures ranging from -50 to 120°C ([0091]), which encompasses the claimed range of “1°C to 50°C,” establishing a prima facie case of obviousness. Shiba further teaches many orders of addition which include the third component of the tertiary catalyst system (e.g., [0094]-[0098]). Shiba then teaches mixing the catalyst system with the monomers any polymerization of the mixture ([0100] and [0103]), and teaches that the temperature of polymerization may range from -30 to 150°C ([0103]), which encompasses the claimed range of “20°C to 125°C,” establishing a prima facie case of obviousness.
Regarding claim 16, Wakefield teaches the production of a polyisoprene (Abstract).
Regarding claim 17, as described above, Wakefield teaches a group of commercially satisfactory inventive polymers having between about 80 and 96% cis-1,4-structures and about 3 to about 10% 3,4-structures (col. 3, lines 31-38). These values overlap the claimed ranges of “”at least 96%” and “at least 5%,” respectively, establishing prima facie cases of obviousness.
Furthermore, Shiba contemplates polymers having cis contents ranging from 93.5 to 99.4% (p. 17), which overlaps the claimed range of “ at least 96%,” establishing a prima facie case of obviousness.
Finally, Wakefield as modified by Shiba and Meng ’16 results in a polyisoprene product which meets the claimed compositional limitations, and which is produced by a substantially identical process as claimed. Products of identical chemical compositions cannot have mutually exclusive properties. Where the claimed and prior art products are identical or substantially identical in structure or composition, a prima facie case of obviousness has been established. See MPEP 2112.01. The claimed molecular structure will inherently be present in the polymer of Wakefield as modified by Shiba and Meng’16, as applied to claim 16, above.
Regarding claim 18, Wakefield teaches the formation of rubber compositions of the inventive polymers including 100 phr of the inventive polymer and 50 parts of carbon black (e.g., col. 27, lines 10-19), which overlap the claimed ranges of “at least 5phr” and “at least 20 phr,” respectively, establishing prima facie cases of obviousness.
Regarding claims 19, Wakefield does not directly disclose compositions wherein the inventive polymer is blended with other rubber polymers. However, Wakefield’s expressed inventive motivation is to produce polyisoprenes which perform comparably to natural rubber (e.g., col. 3, lines 5-9). Wakefield subsequently pronounces the success in doing so within the experimental examples (e.g., col. 22, lines 25-28 and col. 23, lines 11-15). Finally, the obviousness analysis may “take account of the inferences and creative steps that a person of ordinary skill in the art would employ.” KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 421 (2007). For example, the analysis may “include recourse to logic, judgment, and common sense available to the person of ordinary skill that do not necessarily require explication in any reference or expert opinion.” Perfect Web Techs., Inc. v. InfoUSA, Inc., 587 F.3d 1324, 1329 (Fed. Cir. 2009). The Patent Trial and Appeal Board has held that mixing equivalent components in a 1:1 ratio represented no more than application of the “logic, judgment, and common sense available to the person of ordinary skill” in the art. Ex parte Swanzy, Appeal 2017-004875 at 8-9.
In this case, Wakfield discloses the inventive polymer and natural rubber as equivalents. It would have would have been prima facie obvious, using no more than ordinary creativity, logic, judgment, and common sense, to combine the inventive polymer of Wakefield and natural rubber in equal amounts (i.e. in a 1:1 ratio) based on the fact that both are disclosed in parallel as being equally suitable for use in rubber tire formulations. In doing so, the formulations of Wakefield would include 50 phr of natural rubber, 50 phr of the inventive polyisoprene, each of which falls within the claimed ranges of “5 phr to 95 phr,” establishing a prima facie case of obviousness.
Regarding claim 20, Wakefield further discloses the blending of the inventive polyisoprenes together to form a blended rubber composition (col. 24, Example 7). Furthermore, as described above, It would have been obvious to blend the inventive polyisoprenes with natural rubber, as Wakefield expressly confirms their equivalence. A blended sample including two to nine of the inventive polyisoprenes and natural rubber would comprise, according to the formulation of Wakefield, between 10 and about 33.3 phr of the first inventive polymer, and between about 66.6 and 90 parts of the remaining inventive polymers and natural rubber, combined. In each case, these values fall within their respectively claimed ranges, establishing prima facie cases of obviousness.
Response to Arguments
As an initial matter: in the response filed January 16, 2026, Applicant essentially argues that the 102 rejection of the previous office action was improper because the Examiner has referenced evidentiary references (Odian and Stavely) in addition to the anticipating reference Wakefield. Applicant cites MPEP section 2131, which states that anticipation requires that each and every element of a claim in a single prior art reference. However, each and every reference of the previous version of claims 1-11 and 16-17 were present in the single prior art document Wakefield as described in said rejection. Odian and Stavely were merely included as evidentiary references consistent with MPEP 2131.01(III) which supported the technical conclusions that the Examiner described in the 35 USC 102 rejection, and none of the claimed limitations were derived from Odian nor Stavely, nor were any limitations being brought into the disclosure of Wakefield via any alleged obviousness or anticipation mechanisms.
Further regarding Applicant’s arguments with respect to 35 USC 102(a)(1), Applicant argues that the incorporation of Examples within Wakefield containing over 0% trans- isomer content within the inventive polymers disqualifies Wakefield from reading on the newly amended claims which require “substantially zero trans 1,4 isoprene content.” However, as described above and as admitted by the Applicant, Wakefield discloses examples including 0% trans-1,4 isomers (see Applicant’s Remarks, p. 7, fourth paragraph). The incorporation of examples which contain greater than 0% trans- isomer do not rebut the existence of examples which contain 0% trans- isomer. Patents are relevant as prior art for all of the information that they contain, and non-preferred and alternative embodiments nonetheless constitute prior art (see MPEP 2123.I and II). Furthermore, Wakefield specifically teaches polymers having structures overlapping the claimed ranges, as described above. Therefore, Wakefield meets the claimed compositional limitations.
While Applicant’s arguments with regard to 35 USC 102(a)(1) are unpersuasive, Applicant’s amendment of claim 1 disqualifies the rejections of claims 1-11 and 16-17 under 35 USC 102(a)(1). Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Wakefield under 35 USC 103.
Applicant's arguments with respect to 35 USC 103 have been fully considered but they are not persuasive for the same reasons as described above.
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.
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/JOSHUA CALEB BLEDSOE/Examiner, Art Unit 1762
/ROBERT S JONES JR/Supervisory Patent Examiner, Art Unit 1762