DETAILED ACTION
Notice of Pre-AIA or AIA Status
1. The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Status of the Claims
2. Claims 1, 3-15 are currently pending. Claims 10, 12-13 have been previously withdrawn. Claims 1, 3-9, 11 and 14-15 are currently under examination. This office action is in response to the amendment filed on 11/03/2025.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
3. Claim 1-9, 11 and 14-15 are rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention. Concerning claim 1 the claim recites “the content of the structural unit derived from the norbornene compound is 15 mol% or more in the total repeating structural units of the ring-opened copolymer”. Applicants specification paragraph 0030 indicates that the content of the structural unit derived from the norbornene compound is preferably 5 to 95 mol% and additionally indicate that it is more preferably 15 to 85 mol%. This does not provide sufficient support for the claimed indication of 15 mol% or more which includes values above the indicated upper limit of 95 mol% from applicants specification. As such the entire range of “15 mol% or more” is not described in the specification in such a way as to reasonably convey to one skilled in the art that the inventor had possession of the claimed invention as the claimed limitations includes values above 95 mol% which would not be conveyed by the broadest indication of 5 to 95 mol% in paragraph 0030.
Concerning claim 14 the claim recites the content the structural unit derived from the monocyclic olefin is 84.98 mol%. Applicant specification paragraph 0033 gives that the content of the monocyclic olefin structural unit is 4.92 to 94.995 mol% and more preferably 14.93 to 84.98 mol%. This does not provide sufficient support for the claimed indication of 84.98 mol% or less which includes values below the indicated lower limit of 4.92 mol% from applicants specification. As such the entire range of “84.98 mol% or less” is not described in the specification in such a way as to reasonably convey to one skilled in the art that the inventor had possession of the claimed invention as the claimed limitations includes values below 4.92 mol% which would not be conveyed by the broadest indication of 4.92 to 94.995 mol% in paragraph 0033.
Claims 2-9, 11, 15 are rejected as being dependent from a rejected base claim.
Claim Rejections - 35 USC § 103
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 the 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.
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.
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.
4. Claim(s) 1, 3, 5-9,11, and 14-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Starzewski (US 2003/0120011 A1) in view of Tsunogae (US 2012/0296035 A1).
Concerning claim 1, 3, 5-6, 14-15 Starzewski teaches the polymerization of polar substituted norbornenes and/or cycloalkenes characterized in the that the polymerization is carried out in the presence of one or more tungsten carbyne complexes and/or molybdenum carbyne complexes (paragraph 0001) and indicates that tungsten and molybdenum compounds are used as catalysts for ring opening polymerization of substitute norbornenes (paragraph 0003), and that the catalysts used in the polymerization are metathesis catalysts (paragraph 0008) indicating that the polymer formed would be a ring opened polymer.
Starzewski teaches an example of copolymerization of equal molar amounts of 5-cyano-2-norbornene and cyclopentene (paragraph 0113-0117). 5-cyano-2-norbornene has a structure of the claimed formula (I) when one of the R1-R4 groups is a cyano group which is a substituent containing a nitrogen atom and where m is 0.
This exemplary polymer differs from the claimed copolymer only in that it does not have a branched structural unit in the claimed amount of the polymer.
Tsunogae is drawn to ring opening polymers of cyclopentene (abstract) and teaches that using a cyclic olefin having a vinyl group and/or a compound having three or more vinyl groups may also be used for ring opening polymerization to introduce a branch structure the ring opened polymer and that doing so makes it possible to improve the hot flow property of the ring opening polymer (paragraph 0068). Particular examples of the cyclic olefin having a vinyl group include 5-vinylnorbornene (paragraph 0069) and when the cyclic olefin having a vinyl group is used it is preferably used in an amount of from 0.005 to 0.8 mol% of the monomers (paragraph 0071). It should be noted that 5-vinylnorborene would provide a structure of the claimed formula V as the branched structure.
This amount of the branched structure is an overlapping range with the claimed range.
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.
It would have been obvious to one of ordinary skill in the art at the time off filling to alter the exemplary copolymer of Starzewski to include the branched structure of 5-vinyl norbornene as taught by Tsunogae to give the claimed copolymer for the purpose of helping to improve the hot flow property of the ring opening polymer so as to improve handling and manufacturing ability of the copolymer.
Concerning claim 7 Starzewski in view of Tsunogae teaches the copolymer of claim 1 as is stated above.
Starzewski does not explicitly give the claimed range of the weight average molecular weight, however examples of the copolymerization of 5-cyano-2-norbornene with cyclopentene have weight average molecular weights of 128,500 g/mol, 216,000 g/mol , 366,400 g/mol, 397,900 g/mol , 484,500 g/mol (paragraphs 0113-0117). These exemplary values provide an overlapping range with the claimed range of the 150,000 or more and 400,000 or less.
Tsunogae teaches that the weigh average molecular weight of the polymer is from 100,000 to 1,000,000 (abstract) which is also an overlapping range with the claimed range.
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.
It would have been obvious to one of ordinary skill in the art at the time of filling to provide the copolymer of Starzewski in view of Tsunogae with the claimed weight average molecular weight of the copolymer because both Starzewski and Tsunogae teach that overlapping ranges with the claimed range of the weight average molecular weight.
Concerning claim 8 Starzewski further teaches that the polymers can be used for typical rubber applications such as profiled sections or seals and can be used alone or mixed with other polymers such as various rubbers (paragraph 0044).
It would have been obvious to one of ordinary skill in the art at the time of filling to use the claimed copolymer of Starzewski in view of Tsunogae as part of a rubber composition because Starzewski teaches that the copolymers can be used for rubber applications and can be mixed with rubbers.
Concerning claim 9 Starzewski in view of Tsunogae teaches the rubber composition of claim 8 which can include additional rubber.
Starzewski does not specifically teach a crosslinker being present in the rubber composition.
Tsunogae teaches rubber compositions including an additional rubber with the ring opened polymer (paragraph 0098) and teaches that the composition can include additional additives such as crosslinking agents (paragraphs 0099-0100).
It would have been obvious to one of ordinary skill in the art at the time of filling to include a crosslinking agent in the rubber composition of Starzewski in view of Tsunogae as is taught by Tsunogae for the purpose of providing known useful additives to the rubber composition.
Concerning claim 11 Starzewski in view of Tsunogae teaches the rubber composition of claim 8 as is stated above.
Starzewski further teaches that the copolymers can be used for technical articles such as flexible hoses tubing , profiled sections and other components and can be produced by injection molding (paragraph 0044).
It would have been obvious to one of ordinary skill in the art at the time of filling to use the rubber composition of Starzewski in view of Tsunogae to provide a molded article because Starzewski teaches that articles from the copolymer can be made by injection molding.
5. Claim(s) 1, 3-9, 11, 14-15 is/are rejected under 35 U.S.C. 103 as being unpatentable over Smit (US 2015/0218328 A1) in view of Tsunogae (US 2012/0296035 A1).
Concerning claim 1, 3-6 and 14-15 Smit teaches a copolymer which is made by ring opening metathesis polymerization of a monomer a) which is at least one first olefin monomer selected from the group consisting of a cyclic olefin monomer having at least one endocyclic CC double bond where no tertiary carbon atom bearing a hydrogen atom is present in alpha position to the double bond and b) at least one first olefin monomer selected from the group consisting of a cyclic olefin monomer having at least one endocyclic CC double bond where a tertiary carbon atom bearing a hydrogen atom is present in alpha position to the double bond (paragraphs 0006-0008). The monomer a) is preferably cis cyclooctene (paragraph 0023) and the monomer b) is preferably norbornene (paragraph 0024) and the molar ratio of monomer a) to monomer b) is preferably from 50:50 to 80:20 (paragraph 0022).
The amount of polycylic olefin monomer used to produce the copolymer with at least two carbon carbon double bonds is less than 1 mol% and preferably less than 0.8 mol% based on the entirety of the monomers (paragraph 0020).
As this is the only other indicated monomer used in the polymer this would result in the amount of norbornene to range from 49.5 mol% to 19.8 mol% and the amount of cylcooctene to range form 49.5 mol% to 79.8 mol%.
It should be noted that Smit teaches exemplary polymers having molar ratios of 50:50 norbornene to cis cyclo octene and 20:80 norbornene to cis cyclo otene (paragraph 0055 and 0058).
As such the difference between the polymer of Smit and the claimed polymer is that Smit does not teach the claimed content of the branched structural unit.
Tsunogae is drawn to ring opening polymers of cyclopentene (abstract) and teaches that using a cyclic olefin having a vinyl group and/or a compound having three or more vinyl groups may also be used for ring opening polymerization to introduce a branch structure the ring opened polymer and that doing so makes it possible to improve the hot flow property of the ring opening polymer (paragraph 0068). Particular examples of the cyclic olefin having a vinyl group include 5-vinylnorbornene (paragraph 0069) and when the cyclic olefin having a vinyl group is used it is preferably used in an amount of from 0.005 to 0.8 mol% of the monomers (paragraph 0071). It should be noted that 5-vinylnorborene would provide a structure of the claimed formula V as the branched structure and that this amount of a polycyclic olefin monomer having at least two carbon carbon double bonds is within the range indiated by Smit.
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.
It would have been obvious to one of ordinary skill in the art at the time of filling to use the claimed amount of 5-vinyl norbornene in the polymer of Smit because Smit teaches that monomers of this type can be present in an amount that overlaps with the claimed range Tsunogae teaches that providing the branched structure in the claimed amount would help improve the hot flow property of the ring opening polymer.
Concerning claim 7 Smit in view of Tsunogae teaches the copolymer of claim 1 as is stated above.
Smit is silent as to the weight average molecular weight of the copolymer.
Tsunogae teaches that the weight average molecular weight of the polymer is from 100,000 to 1,000,000 (abstract) which is also an overlapping range with the claimed range.
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.
It would have been obvious to one of ordinary skill in the art at the time of filling to use the weight average molecular weight of the ring opening polymer of Tsunogae in the copolymer of Smit in view of Tsunogae to give the claimed weight average molecular weight in order to provide a useful weight average molecular weight of the ring opened copolymer.
Concerning claim 8 Smit in view of Tsunogae teaches the copolymer of claim 1 as is stated above. Smit further teaches that the copolymer is used as part of a rubber material (paragraphs 0033-0035) and can include additional rubbers (paragraph 0032) which would provide a rubber composition comprising the claimed copolymer.
Concerning claim 9 Smit teaches that the rubber composition can include additives (paragraph 0035) and teaches that the copolymer can be attached to a tired carcass via crosslinking (paragraph 0044).
Tsunogae teaches rubber compositions including an additional rubber with the ring opened polymer (paragraph 0098) and teaches that the composition can include additional additives such as crosslinking agents (paragraphs 0099-0100).
It would have been obvious to one of ordinary skill in the art at the time of filling to include a crosslinking agent in the rubber composition of Smit in view of Tsunogae as is taught by Tsunogae for the purpose of providing known useful additives to the rubber composition.
Concerning claim 11 Smit in view of Tsunogae teaches the rubber composition of claim 8 as is stated above. Smit further teaches that the the copolymer is introduced into a rubber containing article preferably a pneumatic tire (paragraph 0034). The pneumatic tire would correspond to the claimed molded article.
Response to Arguments
6. Applicant’s arguments with respect to claim(s) 1, 3-9, 11, 14-15 have been considered but are moot because the new ground of rejection does not rely on any reference applied in the prior rejection of record for any teaching or matter specifically challenged in the argument.
Applicant argues that even if a prima facie case were established it would be rebutted by the strong evidence of non obviousness. As taught in applicants specification this specific compositional range is not an arbitrary selection. It is this combination the low level of branching 0.005 to 0.08 mol% and the high level of the norbornene compound 15 mol% or more that achieves the inventions stated goals as shown in the specifications at paragraphs 0007 and 00030 and demonstrated in Table 1 applicants invention provides excellent hot flowability and can give a crosslinked rubber having excellent wear resistance.
This argument in not found to be persuasive as Tsunogae is drawn to ring opening polymers of cyclopentene (abstract) and teaches that using a cyclic olefin having a vinyl group and/or a compound having three or more vinyl groups may also be used for ring opening polymerization to introduce a branch structure the ring opened polymer and that doing so makes it possible to improve the hot flow property of the ring opening polymer (paragraph 0068). Particular examples of the cyclic olefin having a vinyl group include 5-vinylnorbornene (paragraph 0069) and when the cyclic olefin having a vinyl group is used it is preferably used in an amount of from 0.005 to 0.8 mol% of the monomers (paragraph 0071).
This would indicate that improvement of the hot flow property of the polymer would be an expected property. It should be noted that the references used in the rejections provided above require that that norbornene monomer be present in amounts greater than 15 mol% and as such unexpected results concerning the amount of norbornene monomer can not be used to over come these rejections. Moreover the only example which has a value above the claimed range of the amount of branching structural unit , Comparative example 3, has a value of 0.083 mol% that would be considered to be within the claimed of 0.005 to 0.08 mol% as this value would round to the claimed upper limit of 0.08. Claim language to place this comparative example outside the claimed range would require that the upper limit be 0.080 mol%. More over this polymer is indicated to have a Weight average molecular weight which is almost twice that of the next highest example provided by applicant. Weight average molecular weight would be expected to have a significant effect on the viscosity and hot flow properties of the polymer and a decrease in viscosity and the presence of gelation are not unexpected given higher values of crosslinking monomer such as 5-vinyl -2-norbornene, since as the amount of branching increases the polymer chains would entangle with each other more and gelation would be caused by any irregulars in the concentration of branching with areas of high branching becoming so branched that they form a gel. As such this is not unexpected. Moreover it should be noted that the only data provided is of 5-vinyl -2-norborene which is not in the independent claim and making it unclear if the data is commensurate with the scope of the independent claim. Moreover the lower amounts of the branching unit do not have any data provided making it unclear if the data is commensurate with the scope of the claims.
Dearnaley (US 5,594,041) is drawn to the structural integrity of polymers (abstract) and provides evidence that Increased bonding or crosslinking in polymers generally should increase the hardness fracture resistance softening temperature and abrasive or adhesive wear resistance of the polymer (column 1 lines 35-40). This evidence indicates that the improved wear resistance of the polymer seen in the examples vs the comparative examples is not unexpected as the presence of a branching unit would be expected to result in improved wear resistance.
As such the data which is provided is not found to be sufficient in order to indicate unexpected results and the rejections provided above are maintained.
Conclusion
7. Claims 1, 3-9, 11, 14-15 are rejected. No claims are currently allowable.
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 DAVID L MILLER whose telephone number is (571)270-1297. The examiner can normally be reached M-F 9:30-6:00.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Joseph Del Sole can be reached at 571-272-1130. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/DAVID L MILLER/ Examiner, Art Unit 1763
/JOSEPH S DEL SOLE/Supervisory Patent Examiner, Art Unit 1763