CTNF 18/558,339 CTNF 68156 DETAILED ACTION Notice of Pre-AIA or AIA Status 07-03-aia AIA 15-10-aia 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 07-20-aia AIA 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. 07-20-02-aia AIA 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. 07-21-aia AIA Claim s 1–10 is/are rejected under 35 U.S.C. 103 as being unpatentable over WO 2020/081210 (hereafter WO’210) in view of WO 2020/081208 (hereafter WO’208), further in view of WO 2005/058787 (hereafter WO’787) and Whitman (US 3,337,601, hereafter US’601), and, as to claim 9, further in view of Giacobbe et al. (US 5,112,519, hereafter US’519) . Claim 1. WO’210 teaches lightly branched oligomer products derived from C4-containing feedstocks, including products containing 45 wt.% to 85 wt.% C12 oligomer and 5 wt.% to 55 wt.% C16 oligomers, and also products containing 60 wt.% to 85 wt.% C12 oligomer and 8 wt.% to 20 wt.% C16 oligomers. WO’208 teaches converting the oligomer product to aldehydes and/or alcohols and then converting the oligomer products and alcohols to surfactants, including sulfates. WO’787 teaches a process for producing alcohols by hydroformylating olefins and subsequently hydrogenating the hydroformylation product, and further teaches hydroformylation with carbon monoxide and hydrogen. US’601 teaches reacting alcohol and chlorosulfonic acid and recovering the corresponding alcohol sulfate product. It would therefore have been obvious to convert the lightly branched C12/C16 oligomer feed of WO’210 through the hydroformylation, reduction, and sulfation sequence to obtain the claimed branched alcohol sulfates. WO’210, [0083], lines 566–568; WO’208, [0101], line 621, Elements 31–33; WO’787, lines 129 and 514–515; US’601, lines 205 and 296–306. Claim 2. WO’208 teaches contacting a feedstock comprising at least one C3 to C20 olefin/paraffin under oligomerization conditions in the presence of a Si/Al ZSM-23 catalyst, and further teaches embodiments in which the feed contains at least 40 wt.% C3 olefins/paraffins and embodiments in which the feed contains at least 40 wt.% C4 olefins/paraffins. That disclosure renders obvious the recited use of at least one C3 olefin and/or at least one C4 olefin with a zeolite catalyst to form the claimed oligomer product. WO’208, [0101], line 621, Elements 1, 2, and 4. Claim 3. WO’210 identifies ZSM-23 as an MTT-type zeolite. WO’208 teaches catalyst treatments selected from steaming, acid washing, depositing coke, and combinations thereof. Because claim 3 is written in the alternative, the MTT/ZSM-23 species together with the taught steaming, acid-washing, or coke-deposition treatments is sufficient to render the claim obvious. WO’210, line 58; WO’208, [0101], line 621, Elements 21 and 22. Claim 4. WO’208 teaches that the ZSM-23 catalyst may be an extrudate comprising binder and catalyst and may be produced via crystal growth. US’662 teaches ZSM-23 zeolite in the form of a 1/16-inch cylindrical extrudate consisting of 65% zeolite and 35% alumina binder. Those disclosures render obvious ZSM-23 crystallites and ZSM-23 crystallites defining a shaped catalyst body. WO’208, [0101], line 621, Elements 23 and 24; US’662, lines 601–602. Claim 5. WO’208 teaches oligomerization conditions of 170°C to 270°C and a weight hourly space velocity of 5 hr.^-1 to 30 hr.^-1. Those conditions fall within the broader claimed ranges of about 90°C to about 350°C and about 2 hr.^-1 to about 70 hr.^-1. WO’208, [0101], line 621, Element 25. Claim 6. WO’210 teaches oligomer products containing 45 wt.% to 85 wt.% C12 oligomer and 5 wt.% to 55 wt.% C16 oligomers, and also products containing 60 wt.% to 85 wt.% C12 oligomer and 8 wt.% to 20 wt.% C16 oligomers. Those disclosures necessarily satisfy the requirement for at least about 25 wt.% C10–C13 olefin oligomers. WO’210, [0083], lines 566–568. Claim 7. WO’210 teaches C12 oligomer-containing products derived from C4-containing feedstocks. WO’208 teaches trimers having a branching index of less than 2.1 and expressly discloses branching-index ranges beginning at 1.3. Since the C12 component in the C4-derived system is the trimer fraction, the cited art renders obvious the limitation that the C12 olefin oligomers have an average branching index, as measured by GC, ranging from about 1.3 to about 2.0. WO’210, [0083], lines 566–568; WO’208, [0101], line 349. Claim 8. WO’787 teaches that hydrocobaltcarbonyl, HCo(CO)4, is the active catalyst form and that the initial cobalt species can be dicobalt octacarbonyl, Co2(CO)8. WO’787, lines 142 and 381. Claim 9. US’519 teaches that ZSM23-dodecenes had 1.3 methyl branches on average and that the resulting tridecanols had 1.4 branching methyl groups by proton NMR, nearly the same number as in the feed, and further states that no new branches are created during hydroformylation. That disclosure would have suggested the presently claimed limitation that the C13 branched alcohols have an NMR branching index not more than 0.5 units greater than the branching index of the C12 olefin oligomers. US’519, lines 226–232. Claim 10. US’601 teaches reacting a long-chain aliphatic alcohol with chlorosulfonic acid and continuously recovering the corresponding alcohol sulfate product. Because claim 10 is drafted in the alternative, that teaching is sufficient to render the claim obvious. US’601, lines 205 and 296–306 . 07-21-aia AIA Claim s 11–17 is/are rejected under 35 U.S.C. 103 as being unpatentable over Borowiec et al. (US 7,425,662, hereafter US’662) in view of WO 2020/081210 (hereafter WO’210) in view of WO 2020/081208 (hereafter WO’208), further in view of WO 2005/058787 (hereafter WO’787) and Whitman (US 3,337,601, hereafter US’601), and, as to claim 9, further in view of Giacobbe et al. (US 5,112,519, hereafter US’519) . Claim 11. US’662 teaches butene-derived octenes, dodecenes, and hexadecenes. It also teaches that the trimeric component has Type II olefins at least 20%, preferably 25–45%, Type IVA olefins at least 45%, preferably 45–65%, and Type IVB olefins at most 5%, preferably at most 3%. WO’210 explains that Type IV includes Type IVA and Type IVB. Thus, the cited art teaches a Type II plus Type IV content of at least about 70 wt.%. US’662 further teaches dodecenes having about 1.05 to at most about 1.6 methyl branches, which corresponds to about 0.087 to about 0.133 methyl branches per carbon atom and overlaps the claimed 0.08 to 0.16 range. US’662 also teaches that the low degree of branching and less hindered double-bond structure result in improved oxonation yields to aldehydes and alcohols. WO’208 teaches converting the oligomer product to aldehydes and/or alcohols and then to surfactants including sulfates. WO’787 and US’601 supply the hydroformylation, reduction, and sulfation details. Accordingly, claim 11 would have been obvious. US’662, lines 657–659 and 669–676; WO’210, lines 87–91; WO’208, [0101], line 621, Elements 31–33; WO’787, lines 129 and 514–515; US’601, lines 205 and 296–306. Claim 12. US’662 teaches butene-derived dodecenes and hexadecenes. WO’210 teaches oligomer products containing 45 wt.% to 85 wt.% C12 oligomer and 5 wt.% to 55 wt.% C16 oligomers, and also products containing 60 wt.% to 85 wt.% C12 oligomer and 8 wt.% to 20 wt.% C16 oligomers. WO’208 teaches branching-index ranges for trimers that begin at 1.3. Those disclosures render obvious a method in which at least a majority of the olefin oligomers are C10–C13 oligomers and the C12 olefin oligomers have an average branching index, as measured by GC, ranging from about 1.3 to about 2.0. US’662, line 659; WO’210, [0083], lines 566–568; WO’208, [0101], line 349. Claim 13. WO’210 teaches oligomer products containing 45 wt.% to 85 wt.% C12 oligomer and 60 wt.% to 85 wt.% C12 oligomers. Those disclosures render obvious the limitation that the plurality of olefin oligomers comprises or consists essentially of C10–C13 olefin oligomers. WO’210, [0083], lines 566–568. Claim 14. WO’787 teaches that HCo(CO)4 is the active catalyst form and that the initial cobalt species can be dicobalt octacarbonyl, Co2(CO)8. WO’787, lines 142 and 381. Claim 15. US’519 teaches that the ZSM23-dodecene feed had 1.3 methyl branches on average and that the resulting tridecanols had 1.4 branching methyl groups by proton NMR, nearly the same number as in the feed, and that no new branches are created during hydroformylation. That disclosure renders the branch-retention limitation of claim 15 obvious for the same reasons set forth with respect to claim 9. US’519, lines 226–232. Claim 16. US’662 teaches butene-derived octenes, dodecenes, and hexadecenes. That disclosure renders obvious the limitation that the plurality of olefin oligomers comprises one or more oligomers having about 8 to about 16 carbon atoms. US’662, lines 657–659. Claim 17. US’601 teaches reacting alcohols with chlorosulfonic acid to form alcohol sulfate products and continuously recovering the corresponding alcohol sulfate product. Because the claim is written in the alternative, that teaching is sufficient. US’601, lines 205 and 296–306 . 07-21-aia AIA Claim s 18–26 is/are rejected under 35 U.S.C. 103 as being unpatentable over Borowiec et al. (US 7,425,662, hereafter US’662) in view of WO 2020/081210 (hereafter WO’210) in view of WO 2020/081208 (hereafter WO’208), further in view of WO 2005/058787 (hereafter WO’787) and Whitman (US 3,337,601, hereafter US’601), and, as to claims 22–26, further in view of Killebrew et al. (US 5,849,960, hereafter US’960), Tang (US 2017/0137747, hereafter US’747), Edwards (US 6,706,931, hereafter US’931), OECD Test No. 301, and Federle et al. (US 8,933,131, hereafter US’131) . Claim 18. US’662 teaches butene-derived olefin oligomers including octenes, dodecenes, and hexadecenes. It further teaches that the trimeric component has Type II olefins at least 20%, preferably 25–45%, Type IVA olefins at least 45%, preferably 45–65%, and Type IVB olefins at most 5%, preferably at most 3%. WO’210 explains that Type IV includes Type IVA and Type IVB. Thus, the cited art teaches a Type II plus Type IV content of at least about 70 wt.%. US’662 also teaches dodecenes having about 1.05 to at most about 1.6 methyl branches, corresponding to about 0.087 to about 0.133 methyl branches per carbon atom, and teaches that the low branching and less hindered double-bond structure improve oxonation to aldehydes and alcohols. WO’208 teaches that the oligomer product can be used as feed for hydroformylation to aldehydes and/or alcohols and then to surfactants including sulfates. WO’787 teaches hydroformylation and hydrogenation to alcohols, and US’601 teaches sulfation with chlorosulfonic acid to obtain alcohol sulfate products. It therefore would have been obvious to prepare the branched alcohol sulfate composition of claim 18 from the lightly branched C8/C12/C16 oligomer feed taught by US’662 through the hydroformylation, reduction, and sulfation sequence taught by the remaining references. US’662, lines 657–659 and 669–676; WO’210, lines 87–91; WO’208, [0101], line 621, Elements 31–33; WO’787, lines 129 and 514–515; US’601, lines 205 and 296–306. Claim 19. WO’210 teaches oligomer products derived from C4/C5 feedstocks containing 60 wt.% to 85 wt.% C12 oligomer and 8 wt.% to 20 wt.% C16 oligomers. WO’208 teaches trimers with branching indices less than 2.1 and within ranges beginning at 1.3. Those disclosures render obvious the limitation that at least the C12 olefin oligomers have an average branching index, as measured by GC, ranging from about 1.3 to about 2.0. WO’210, [0083], lines 566–568; WO’208, line 349. Claim 20. WO’210 teaches C4-derived oligomer products containing 45 wt.% to 85 wt.% C12 oligomer and C4/C5-derived products containing 60 wt.% to 85 wt.% C12 oligomers. Since C12 oligomer falls within the recited C10–C13 range, those disclosures render obvious the limitation that the plurality of olefin oligomers comprises or consists essentially of C10–C13 olefin oligomers. WO’210, [0083], lines 566–568. Claim 21. US’662 teaches butene-derived octenes, dodecenes, and hexadecenes. That disclosure renders obvious the limitation that the plurality of olefin oligomers comprises one or more oligomers having about 8 to about 16 carbon atoms. US’662, lines 657–659. Claim 22. US’960 teaches that highly branched primary alcohol compositions can be sulfated to provide surfactant compositions exhibiting biodegradability. OECD Test No. 301 states that the ready-biodegradability methods include Manometric Respirometry, that the pass level for respirometric methods is 60% of ThOD or ThCO2, and that the pass value must be reached within a 10-day window within the 28-day test period. In view of that teaching, it would have been obvious to evaluate the claimed branched alcohol sulfates under OECD 301F and to expect satisfaction of the corresponding 60%/10-day-window criterion. US’960, col. and line citations as previously noted of record; OECD Test No. 301, lines 3723–3726. Claim 23. US’747 teaches branched, unalkoxylated C6–C14 alkyl sulfate surfactants and teaches that the branched alkyl moieties are preferably characterized by a weight average carbon number ranging from about 9 to about 14, more preferably from about 10 to about 13, and most preferably from about 11 to about 13. The same reference further teaches preferred BAS mixtures including a C12 BAS surfactant and a C13 BAS surfactant, and most preferably mixtures consisting of or consisting essentially of the C12 and C13 BAS surfactants. Those disclosures render obvious a composition in which at least a majority of the branched alcohol sulfates are C11–C14 alcohol sulfates. US’747, lines 197–198 and 213–214. Claim 24. US’747 teaches the C11–C14-centered branched alkyl sulfate composition applied in claim 23. US’931teaches sulfated branched primary alcohol products and states that neutralization and solvent removal produced an approximately 25 weight percent active solution of the desired sulfated products, with the products being clear fluid pale-yellow liquids, and identifies Example A as C12-1 PDOS and Example B as C14-1 PDOS. US’931 further teaches that the sulfates of the branched ether primary alcohols exhibit Krafft temperatures of 10°C or less, more preferably 0°C or less, and are highly soluble in aqueous wash media. Those disclosures would have suggested that closely related C11–C14 branched sulfate surfactants possess aqueous solubility of about 20 wt.% or greater at 25°C. US’747, lines 197–198 and 213–214; US’931, lines 1450–1452 and 972–973. Claim 25. US’747 expressly teaches that the cleaning composition may also include one or more linear alkylbenzene sulphonate surfactants, particularly C10–C20 LAS, and identifies preferred C11–C18 and C11–C14 LAS materials. That disclosure renders obvious the further inclusion of linear alkylbenzene sulfonate in the branched alcohol sulfate composition of claim 18. US’747, lines 514–518. Claim 26. US’747 teaches that the weight ratio of BAS surfactants to LAS surfactants is preferably from about 2:1 to about 1:2. Expressed in the inverse form recited in claim 26, that corresponds to an LAS:branched alcohol sulfate ratio of about 0.5:1 to about 2:1, which falls within the claimed range. US’131 further provides examples containing 5.0 wt.% HLAS and 20 wt.% scattered-branched alcohol sulfate, and 5.5 wt.% linear alkylbenzene sulfonate with 8.9 wt.% scattered-branched chain alcohol sulfates, both of which fall within the claimed ratio range. Those disclosures render the claimed LAS:branched alcohol sulfate ratio obvious. US’747, lines 519–520; US’131, lines 2286–2292 and 2352–2356. Any inquiry concerning this communication or earlier communications from the examiner should be directed to DEBORAH D CARR whose telephone number is (571)272-0637. The examiner can normally be reached Monday-Friday (10:30 am -6:30 pm). 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, Renee Claytor can be reached at 572-272-8394. 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. /DEBORAH D CARR/ Primary Examiner, Art Unit 1691 Application/Control Number: 18/558,339 Page 2 Art Unit: 1691 Application/Control Number: 18/558,339 Page 3 Art Unit: 1691 Application/Control Number: 18/558,339 Page 4 Art Unit: 1691 Application/Control Number: 18/558,339 Page 5 Art Unit: 1691 Application/Control Number: 18/558,339 Page 6 Art Unit: 1691 Application/Control Number: 18/558,339 Page 7 Art Unit: 1691 Application/Control Number: 18/558,339 Page 8 Art Unit: 1691 Application/Control Number: 18/558,339 Page 9 Art Unit: 1691 Application/Control Number: 18/558,339 Page 10 Art Unit: 1691 Application/Control Number: 18/558,339 Page 11 Art Unit: 1691 Application/Control Number: 18/558,339 Page 12 Art Unit: 1691
Prosecution Insights