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 .
Specification
Applicant is reminded of the proper language and format for an abstract of the disclosure.
The abstract should be in narrative form and generally limited to a single paragraph on a separate sheet within the range of 50 to 150 words in length. The abstract should describe the disclosure sufficiently to assist readers in deciding whether there is a need for consulting the full patent text for details.
The language should be clear and concise and should not repeat information given in the title. It should avoid using phrases which can be implied, such as, “The disclosure concerns,” “The disclosure defined by this invention,” “The disclosure describes,” etc. In addition, the form and legal phraseology often used in patent claims, such as “means” and “said,” should be avoided.
The abstract of the disclosure is objected to because the implied phrases "the disclosure relates to" in line 1 and "disclosed herein" is in the second to last line. A corrected abstract of the disclosure is required and must be presented on a separate sheet, apart from any other text. See MPEP § 608.01(b).
Claim Objections
Claim 10 is objected to because of the following informalities: claim 10 states “The method of any one of claim 8” and should read “The method of claim 8.” Appropriate correction is required.
Claim Rejections - 35 USC § 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, 5-7, 11, 14-15, 17, and 19-20 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Robert et al, US20100252156A1.
Regarding claims 1-2, 15, 17, and 19, Robert teaches a block copolymer of a diene elastomer and a polyether, abstract. The first block is a living diene elastomer and the second block is an epoxy functional polyether, shown in formula I, ¶[0023]. The epoxy functional polyether reads on the claimed second block being derived from an epoxide. Additionally, the polyether backbone produced by the epoxy functional polyether is not patentably differentiated from one derived from an epoxide such as ethylene oxide.
Robert teaches in example 1, the A block polymer is made from the polymerization of styrene and butadiene, ¶[0121], which anticipates claims 2 and claim 15. The second block is derived from poly(ethylene glycol)diglycidyl ether ¶[0123]. The molecular weight of the first block, polymer A, is 75,000 g/mol ¶[0122], anticipating claim 17. The molecular weight of the poly(ethylene glycol)diglycidyl ether which makes up the second block is 526 g/mol, ¶[0123], which anticipates the molecular weight range for claim 19.
Regarding claims 5-6, and 20, Robert teaches a rubber composition comprising the block copolymer and the fillers of silica and carbon black, where said rubber composition is for a tire, abstract, ¶¶[0055, 0060] and see composition example 1 table of ingredients, ¶[0241], where silica and the carbon black N234 are listed.
Regarding claims 7, 11, and 14, Robert teaches a method of making the copolymer comprising polymerizing the first alkene block of styrene and butadiene with an n-butyllithium initiator in cyclohexane solvent in example 1 polymer A, ¶[0121], which reads on claim 11. Then the epoxide, poly(ethylene glycol)diglycidyl ether, is then injected into the reactor with the polymerized diene, ¶[0123], where it is then reacted for 60 minutes ¶[0124]. When the copolymer is complete, it is separated from solution (the solvents) by steam stripping, drying on an open mill, and drying in an oven, ¶[0126], which reads on claim 14.
Regarding claim 16, Robert teaches the diene portion of the block polymer where it is comprised of butadiene-styrene copolymers has a Tg of 0°C to -70°C ¶[0035]. Robert is silent as to the exact Tg of the final block copolymers, but compares the inventive copolymers to SBR copolymers with a Tg of -38°C, see examples ¶[0239-0240, 0255]. Therefore, it would be obvious to one of ordinary skill in the art before the effective filing date of the claimed invention that the inventive copolymers of Robert would have a similar Tg because the inventive copolymers are to replace the comparative examples that do not have the polyether functionality and additionally, they are going into tire formulations which benefit from low Tg rubber components.
Claims 1-3, 7, 11-15, 17-18 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Laskowski et al, US20190322788A1.
Regarding claims 1-3, 15, 17-18, Laskowski teaches block copolymers comprising blocks derived from alkenes such as styrene, butadiene, and isoprene, ¶¶[0012, 0014], and blocks derived from cyclic monomers such as epoxides, ¶[0019]. Specifically, Laskowski teaches a poly(isoprene-styrene-ethylene oxide) block copolymer PI-PS-PEO in example 5 ¶[0086]. The alkenes of styrene and isoprene read on claims 2 and 15. In Table 6 ¶[0091], the compositions are listed for different permutations of example 5, the sample ID PE-5C has 8.2 wt.% ethylene oxide in the copolymer, which anticipates claim 18. That same sample is comprised of 32.8% isoprene units and 59.1% styrene units and has a molecular weight of 101,000 g/mol, Table 6. Which means the isoprene block is 33,128 g/mol and the styrene block is 59,691 g/mol, both of which individually and together read on the range of claim 17.
Additionally, in example 4 ¶[0111], the block copolymer poly(propylene oxide-styrene-isoprene-styrene-propylene oxide) (PSISP) is produced with propylene oxide ¶[0112], which reads on claim 3.
Regarding claims 7, and 11-14, Laskowski teaches in the preparatory example 2 ¶[0075] and in example 4, ¶[0111], a method of making the PSISP block copolymer. First the dienes of styrene and isoprene are polymerized in the prep example 2 ¶[0076]. The hydroxyl functional triblock copolymer is formed and separated from solution, ¶[0077], which reads on step a of claim 7 and the alkenes of claim 11. The hydroxyl functional triblock polymer is then used in example 4 ¶[0112], where it is dissolved in benzene, phosphazene is added, propylene oxide and triisobutyl aluminum catalyst is added and sealed to react at room temperature, ¶[0112]. The TIBA reads on the organoaluminum catalyst of claims 12-13. The copolymer is then recovered as a solid by rotary evaporation and freeze dried to yield a white powder, ¶[0113], which reads on claim 14.
Claims 1-2, 4, 15, 17, 19 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Kruka et al, US3910856A.
Regarding claims 1-2, 4, 15, 17, 19, Kruka teaches an AB block copolymer of polybutadiene and ethylene oxide in example IV, Col. 6 lines 23-30. The ethylene oxide has an average molecular weight of 2,000 g/mol which reads on claim 19. Kruka states the example follows the process of example I, which states that the polybutadiene block is 715,000 g/mol, Col. 5 lines 50-51, and reads on claim 17. This PB-b-PEO copolymer reads on the formula of claim 4 where X is a combination of the three groups because of the possible cis, trans, 1,2 and 1,4 additions when 1,3-butadiene is homopolymerized. R2 and R3 are hydrogens, R1 is methyl and because the molecular weight is 715,000 g/mol, the repeat unit n is about 13,241 which falls within the claimed range. This is calculated from 715,000/54 where 54 g/mol is the approximate molecular weight of the repeat unit. The ethylene oxide repeat unit, m, is 2000/44 = approximately 45, which also anticipates the claimed range.
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.
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.
Claims 3, 8-10 are rejected under 35 U.S.C. 103 as being unpatentable over Robert et al, US20100252156A1.
Regarding claim 3, Robert teaches the invention according to claim 1 as explained above. Robert exemplifies poly(ethylene glycol)diglycidyl ether in the examples, ¶[0123], but also teaches in the disclosure that the alkylene radical in formula 1 is a C1-C10 radical, ¶[0026], and lists examples of epoxy functional polypropylene ethers such as polypropylene glycol monoglycidyl monobutyl ether and polypropylene glycol diglycidyl ether ¶[0029], which reads on the propylene oxide units of claim 3.
It is prima facie obvious to substitute one material for another to obtain predictable results when the materials fulfill the same use and function. “[I]t is prima facie obvious to substitute equivalents, motivated by the reasonable expectation that the respective species will behave in a comparable manner or give comparable results in comparable circumstances.” In re Ruff 118 USPQ 343; In re Jezel 158 USPQ 99; “the express suggestion to substitute one equivalent for another need not be present to render the substitution obvious.” In re Font, 213 USPQ 532.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the poly(ethylene glycol)diglycidyl ether in example 1 for an epoxy functional polypropylene glycol such as polypropylene glycol diglycidyl ether as the functionalizing agent to react with the polymerized diene block with the motivation of obtaining another permutation of a block copolymer of a diene and polyether as taught by Robert.
Regarding claims 8-10, Robert teaches the invention according to claim 7 as explained above. Robert further teaches that several types of polar agents may be used in the polymerization of the alkene, such as the non-chelating agent THF, and chelating agents such as tetramethylethylenediamine (TMEDA), ¶[0038], which reads on the claimed multidentate ligand. In example 1, Robert exemplifies THF as the polar agent in combination with the n-butyllithium initiator and cyclohexane solvent, ¶[0122], which reads on the initiator of claim 9.
It is prima facie obvious to substitute one material for another to obtain predictable results when the materials fulfill the same use and function.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to substitute the THF in example 1 for the TMEDA as the polar agent with the motivation of obtaining another permutation of a polymerized diene block of styrene and butadiene as taught by Robert.
Claims 7 and 11-12, are rejected under 35 U.S.C. 103 as being unpatentable over Kruka et al, US3910856A.
Regarding claims 7 and 11, Kruka teaches a process for making the block copolymer of example IV, which contains polybutadiene, by repeating the process of example I, Col. 6 line 23 and Col. 5 lines 40-50. The process of example I has the styrene polymerized before the butadiene, so for example IV this implies that the process is such that the ethylene oxide is polymerized first and then the butadiene is added. But Kruka further teaches in the broader disclosure that generally the diene, such as butadiene, is polymerized first to form the first block in the presence of a lithium catalyst, then the co-polymerizable monomer (which is what the ethylene oxide is in example IV) is injected and polymerization is continued until the AB block copolymer is formed, Col. 4 lines 22-40.
It would have been obvious to one having ordinary skill in the art at the time the invention was made to have polymerized the butadiene in example IV first and then polymerized the ethylene oxide in the presence of the polybutadiene block because the selection of any order of steps has been held to be prima facie obvious. See In re Burhans, 154 F.2d 690, 69 USPQ 330 (CCPA 1946) which states that selection of any order of performing process steps is prima facie obvious in the absence of new or unexpected results.
Regarding claim 12, Kruka further teaches using organoaluminum catalysts for the formation of the block copolymer, Col. 4 lines 56-57.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to VIRGINIA L STONEHOCKER whose telephone number is (571)272-3431. The examiner can normally be reached Monday-Friday 7:00AM-4:00PM EST.
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, Randy Gulakowski can be reached at 571-272-1302. 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.
/V.L.S./Examiner, Art Unit 1766
/MARC S ZIMMER/Primary Patent Examiner, Art Unit 1765
Prosecution Insights