Alan Stern et al.

Patent Trials and Appeals Board

Jan 3, 2022

2021002184 (P.T.A.B. Jan. 3, 2022)

UNITED STATES PATENT AND TRADEMARK OFFICE UNITED STATES DEPARTMENT OF COMMERCE United States Patent and Trademark Office Address: COMMISSIONER FOR PATENTS P.O. Box 1450 Alexandria, Virginia 22313-1450 www.uspto.gov APPLICATION NO. FILING DATE FIRST NAMED INVENTOR ATTORNEY DOCKET NO. CONFIRMATION NO. 12/441,844 03/18/2009 Alan J. Stern 81,689 5703 168382 7590 01/03/2022 Indorama Ventures Oxides LLC 24 Waterway Avenue, Suite 1100 The Woodlands, TX 77380 EXAMINER BROWN, COURTNEY A ART UNIT PAPER NUMBER 1617 NOTIFICATION DATE DELIVERY MODE 01/03/2022 ELECTRONIC Please find below and/or attached an Office communication concerning this application or proceeding. The time period for reply, if any, is set in the attached communication. Notice of the Office communication was sent electronically on above-indicated "Notification Date" to the following e-mail address(es): US.Mail@smartbiggar.ca edward.korompai@us.indorama.net pwarchambault@smartbiggar.ca PTOL-90A (Rev. 04/07) UNITED STATES PATENT AND TRADEMARK OFFICE BEFORE THE PATENT TRIAL AND APPEAL BOARD Ex parte ALAN J. STERN, R. SCOTT TANN, and CURTIS M. ELSIK1 Appeal 2021-002184 Application 12/441,844 Technology Center 1600 Before ERIC B. GRIMES, ULRIKE W. JENKS, and JOHN E. SCHNEIDER, Administrative Patent Judges. GRIMES, Administrative Patent Judge. DECISION ON APPEAL This is an appeal under 35 U.S.C. § 134(a) involving claims to an herbicidal composition, which have been rejected as obvious. We have jurisdiction under 35 U.S.C. § 6(b). We AFFIRM. 1 Appellant identifies the real party in interest as Indorama Ventures Oxides LLC. Appeal Br. 3. “Appellant” refers to “applicant” as defined in 37 C.F.R. § 1.42. Appeal 2021-002184 Application 12/441,844 2 STATEMENT OF THE CASE Appellant’s “invention relates . . . to the field of a stable chemical formulation[] comprising a slightly water soluble ingredient.” Spec. ¶ 3. “In an embodiment, a formulation comprises a slightly water soluble ingredient and a dispersant. The formulation may be formulated as a suspension concentrate (SC) or a suspoemulsion (SE) formulation.” Id. ¶ 15. “In one embodiment, the ingredient is a slightly water soluble phenoxy herbicide. A phenoxy herbicide refers to members of a family of chemicals related to the growth hormone indoleacetic acid.” Id. ¶ 17. “The dispersant comprises a water soluble derivative of an alternating copolymer or salt thereof.” Id. ¶ 20. “In some embodiments, the dispersant is a styrene/methacrylic acid copolymer.” Id. Claims 9, 10, 14, 15, 23, 24, 26, 27, and 30 are on appeal. Claim 9, reproduced below, is illustrative: 9. A composition comprising: from about 5 w/wt. % to about 55 w/wt. %, based on the total weight of the composition, of a slightly water soluble phenoxy herbicide selected from 2,4-dichlorophenoxyacetic acid; 2,4-dichlorophenoxy propionic acid; 2,4-dichlorophenoxy butyric acid; 2,4,5-trichlorophenoxyacetic acid; 2-methyl-4- chlorophenoxyacetic acid; 2-methyl-4-chlorophenoxy propionic acid; 2-methyl-4-chlorophenoxy butyric acid; and combinations thereof; and from about 0.5 w/wt.% to about 2.0 w/wt%, based on the total weight of the composition, of a dispersant; wherein the dispersant comprises a water soluble derivative of a copolymer or a salt thereof, wherein the copolymer comprises a residue of a first comonomer and a residue of a second comonomer, and wherein the first comonomer comprises an α,β-unsaturated oxyacid, or an Appeal 2021-002184 Application 12/441,844 3 anhydride or derivative thereof, and wherein the second comonomer comprises an olefinic compound containing a species selected from the group consisting of vinyl ethers and esters, internal olefins, allylic alcohols and their corresponding ester derivatives, allylic ethers, allylic halo compounds, allylic aryl compounds, vinyl amides, vinyl chlorides, vinylidene chlorides, and combinations thereof, and wherein the composition is an aqueous suspension concentrate or suspoemulsion composition. Appeal Br. 17 (Claims App.). OPINION Claims 9, 10, 14, 15, 23, 24, 26, 27, and 30 stand rejected under 35 U.S.C. § 103(a) as obvious based on Kirby2 and Crooks.3 Non-Final Act.4 6. The Examiner finds that Kirby teaches “a method of dispersing an insoluble material in an aqueous solution” using a dispersant comprising a copolymer in which “the first comonomer comprises alpha beta-unsaturated oxyacids or anhydrides and [the] second comonomer comprises olefinic compounds containing one or more polymerizable double bonds.” Id. at 7. The Examiner finds that Kirby teaches that water-insoluble materials that can be used in suspension concentrate (SC) formulations include various herbicides, but Kirby does not specifically disclose phenoxy herbicides. Id. at 8-10. The Examiner finds, however, that Crooks discloses an aqueous suspension of nanoparticles comprising an amphiphilic compound and a 2 Kirby et al., US 2005/0101724 A1, published May 12, 2005. 3 Crooks et al., US 2003/0013799 A1, published Jan. 16, 2003. 4 Office Action mailed Dec. 27, 2019. Appeal 2021-002184 Application 12/441,844 4 water-insoluble agrochemical active ingredient, which can be a phenoxyacetic acid such as 2,4-D.5 Id. at 10-11. The Examiner concludes that it would have been obvious to combine Kirby’s method of dispersing a water-insoluble material in an aqueous solution with a phenoxy herbicide such as 2,4-D because Crooks teaches that 2,4-D is a water-insoluble agrochemical active agent. Id. at 11. “Thus, the instant claims would have been obvious because the substitution of one known insoluble active agrochemical for another insoluble active agrochemical in an agrochemical composition would have yielded predictable results.” Id. at 11-12. We agree with the Examiner’s fact-finding and conclusion. Kirby teaches that “the use of a range of derivatisations of alternating copolymers of an α,β-unsaturated oxyacid and an olefin having one or more polymerizable double bonds provides improved dispersibilty [sic] and suspensibility in agrochemical formulations.” Kirby ¶ 10. “Copolymers with substantially regularly spaced anionic charges along the polymer molecule provide advantageous dispersant performance.” Id. ¶ 37. Kirby teaches that “preferred first comonomers include fumaric acid, maleic acid and anhydrides, . . . acrylic and methacrylic acids, esters and amides,” etc. Id. ¶ 40. By comparison, Appellant’s Specification states that “examples of suitable first comonomers include fumaric acid, maleic acid and anhydrides, . . . acrylic and methacrylic acids and the corresponding esters and amides derived thereof,” etc. Spec. ¶ 21. 5 Appellant’s Specification refers to 2,4-dichlorophenoxyacetic acid as “2,4- D acid.” Spec. ¶ 37. Appeal 2021-002184 Application 12/441,844 5 Kirby teaches that “preferred second comonomers include styrene and its alkyl and halo derivatives,” etc. Kirby ¶ 41. By comparison, Appellant’s Specification states that “examples of second comonomers include styrene and alkyl and halo derivatives thereof,” etc. Spec. ¶ 22. Kirby states that, “[i]n agrochemical applications, a wide variety of insoluble materials such as active principals are delivered in aqueous suspension. . . . Water insoluble materials which may advantageously be used in . . . SC [suspension concentrate] formulations include herbicides, insecticides,” etc. Kirby ¶ 55. “Examples of such actives commonly granulated or made as powders in agriculture include: triazine herbicides . . . , urea herbicides. . . , sulphonyl urea herbicides . . . , sulphonanilide herbicides,” etc. Id. Kirby does not expressly suggest formulating phenoxy herbicides with its comonomer dispersants, but Crooks discloses “an aqueous suspension of nanoparticles,” where the “[n]anoparticles . . . comprise an amphiphilic compound and at least an organic water-insoluble agrochemical active ingredient.” Crooks ¶¶ 22, 29. “Examples of organic water-insoluble agrochemical active ingredient include: . . . herbicides, for example selected from . . . phenoxyacetic acids such as 2,4-D.” Id. ¶¶ 33-36. Thus, it would have been obvious to use 2,4-D as the agrochemical active agent in Kirby’s composition comprising an alternating copolymer dispersant because Kirby suggests that a wide variety of water-insoluble herbicides are suitable for use with its dispersant, and Crooks teaches that 2,4-D is a water-insoluble herbicide. Appeal 2021-002184 Application 12/441,844 6 Appellant argues that the rejection is based on hindsight, because Crooks discloses aqueous suspensions that include nanoparticles comprising a solid core of an agricultural active ingredient and the amphiphilic compound surrounding the core. Crooks et al. at [0027]. Appellant respectfully submits one skilled in the art would not have simply taken the agricultural active ingredient 2,4-D disclosed in Crooks et al., added it to Kirby et al. and then reasonably expected a usable aqueous suspension concentrate would be produced. Instead, one skilled in the art would have expected that the active ingredient 2,4-D in the form of the nanoparticles described above would have to be added to Kirby et al. to produce a usable suspension concentrate. Appeal Br. 12-13. This argument is unpersuasive, because Kirby and Crooks disclose alternative methods of making a stable aqueous suspension of a water- insoluble active agent. Crooks’ suspension comprises nanoparticles of an amphiphilic compound and a water-insoluble active ingredient. Crooks ¶¶ 22-24. Crooks states that it is believed that the nanoparticles . . . comprise a solid core of the organic water-insoluble agrochemical active ingredient, and the amphiphilic compound around said core, the hydrophobic moiety interacting with the surface of the core, and the hydrophilic moiety interacting with water, or being at least partially dissolved in water. Id. ¶ 27. Kirby, on the other hand, states that “[t]he alternating, or substantially alternating character, of the copolymers is believed to be critical to [its] invention.” Kirby ¶ 35. Kirby states that “it appears that the alternating character of the copolymer derivatives provides either a consistent and Appeal 2021-002184 Application 12/441,844 7 regular charge density or a steric barrier to aid dispersant performance and also afford improved water solubility.” Id. ¶ 42. Thus, the cited references disclose alternative approaches to improving the dispersibility of a water-insoluble active agent in an aqueous suspension. Appellant has not persuasively explained what would have led a skilled artisan to expect that dispersing 2,4-D in an aqueous suspension would require both Crooks’ nanoparticle-forming amphiphilic compound and Kirby’s copolymer derivative. Appellant also argues that Kirby does not disclose or suggest an aqueous suspension containing 0.5-2 w/wt.% of a copolymer dispersant, as recited in Appellant’s claims, because “Kirby et al. teaches the aqueous suspension concentrate must contain the dispersant in an amount greater than 2.0 w/wt. % (i.e. 3 w/wt.%) in order for it to be usable. Kirby et al. at [0129]-[0130].” Appeal Br. 13. This argument is also unpersuasive, for two reasons. First, Appellant appears to be interpreting the numbers in the ingredient list of paragraph 129 as being in units of wt%, but (a) the list does not indicate that the numbers are in wt% (cf. Kirby ¶ 125) and (b) the total of the numbers is 64.5, not 100 as it would be for ingredients set out by wt%. Id. ¶ 129. Second, the cited paragraphs describe “[a]n Atrazine 900 g/Kg SC formulation” comprising, among other things, “ATLOX 4896A” and “DISPERSANT.” Id. Appellant appears to be interpreting the “ATLOX 4896A” as dispersant (because its amount is listed as “3”) but Kirby states that “[t]he dispersant used was the sodium salt of an alternating copolymer of alphamethylstyrene and maleic anhydride. The SC was prepared by Appeal 2021-002184 Application 12/441,844 8 dissolving the monoethylene glycol, ATLOX 4896A . . . and DISPERSANT in 85% of the water and adding the Atrazine.” Id. ¶ 130. Thus, the dispersant in the cited composition is the “DISPERSANT,” with an amount of “2,” not the “ATLOX 4896A,” with an amount of “3.” Finally, Appellant argues that the Specification shows evidence of unexpected results for the claimed composition. Appeal Br. 14. In particular, as demonstrated in Examples 1-4 of the present application, Appellant has surprisingly found when the slightly water soluble phenoxy herbicide 2,4-D is combined with from about 1.1 w/wt.% to about 1.3 w/wt.%, based on the total weight of the composition, of a water soluble derivative of a copolymer dispersant or a salt thereof to form an aqueous suspension concentrate composition, such composition exhibited no Ostwald Ripening after 45 days of storage. Id.6 Appellant argues that one skilled in the art, when reading Kirby et al. and Crooks et al. in their entirety, would not have expected that combining a slightly water soluble phenoxy herbicide with such a low amount of dispersant as recited in independent claims 9 and 27 would produce an aqueous suspension concentrate that exhibited no Ostwald Ripening (and therefore is physically stable) over such a long period of time. Id. at 15. “One way for a patent applicant to rebut a prima facie case of obviousness is to make a showing of ‘unexpected results.’” In re Soni, 54 F.3d 746, 750 (Fed. Cir. 1995). We have considered Examples 1-4 in 6 “A major drawback of formulating a slightly water soluble ingredient as an aqueous SC is Ostwald ripening, which refers to instances in which the larger crystals of the ingredient grow while the smaller crystals dissolve. Physical instability is one manifestation of Ostwald ripening.” Spec. ¶ 6. Appeal 2021-002184 Application 12/441,844 9 Appellant’s Specification but conclude that they do not demonstrate that the composition of claim 9 would have been nonobvious. Appellant points to the Specification’s Examples 1-4 as evidence of unexpected results. Appeal Br. 4. Those examples show suspension concentrate (SC) formulations comprising, among other components, “2,4-D Acid Tech” (40.7 or 48.4 wt%) and “TERSPERSE® 2700 Dispersant” (1.1 or 1.3 wt%). Spec. ¶ 34. “TERSPERSE® 2700 dispersant is a styrene/methacrylic acid copolymer that is commercially available from Huntsman Corporation.” Id. ¶ 26. The Specification states that “[a]n unexpected result of the formulation comprising the dispersant with a slightly water soluble ingredient is that the formulation is stable. Moreover, Ostwald ripening is reduced or completely eliminated.” Id. ¶ 31. However, “evidence of unexpected results must establish that there is a difference between the results obtained and those of the closest prior art, and that the difference would not have been expected by one of ordinary skill in the art at the time of the invention.” Bristol-Myers Squibb Co. v. Teva Pharms. USA, Inc., 752 F.3d 967, 977 (Fed. Cir. 2014). Here, the closest prior art composition would appear to be that of Kirby’s Example 41, which comprises atrazine (instead of 2,4-D) and “the sodium salt of an alternating copolymer of alphamethylstyrene and maleic anhydride” as dispersant. Kirby ¶¶ 129-130. Kirby’s alphamethylstyrene/ maleic anhydride copolymer appears to meet the requirements of the dispersant in Appellant’s claim 9. See Spec. ¶¶ 21-22 (suitable first comonomers include “maleic acid and anhydrides” and suitable second comonomers include “styrene and alkyl and halo derivatives thereof”). Appeal 2021-002184 Application 12/441,844 10 The comparative compositions in Appellant’s Specification, however, include 2,4-D and “TERSPERSE® 2425,” “TERSPERSE® 2500,” or “TERSPERSE® 2200” as dispersant. Spec. ¶ 37 (Table 2). The Specification does not describe TERSPERSE® 2500 but states that “TERSPERSE® 2425 dispersant is an alkyl naphthalene sulfonate formaldehyde condensate polymer” and “TERSPERSE® 2200 dispersant is an aryl phenol ethoxy phosphate ester, acid copolymer.” Id. ¶ 26. Thus, the Specification does not appear to provide a comparison to the closest prior art composition. In addition, “[e]vidence of secondary considerations must be reasonably commensurate with the scope of the claims.” In re Huai-Hung Kao, 639 F.3d 1057, 1068 (Fed. Cir. 2011). Here, the compositions of Examples 1-4 in the Specification are limited to TERSPERSE® 2700 (a styrene/methacrylic acid copolymer) as the dispersant, used in amounts of 1.1 or 1.3 wt%. Claim 9, by contrast, encompasses amounts of dispersant from “about 0.5 w/wt.% to about 2.0 w/wt%,” and any dispersant that is a water soluble derivative of a copolymer or a salt thereof, wherein the copolymer comprises a residue of a first comonomer and a residue of a second comonomer, and wherein the first comonomer comprises an α,β-unsaturated oxyacid, or an anhydride or derivative thereof, and wherein the second comonomer comprises an olefinic compound containing a species selected from the group consisting of vinyl ethers and esters, internal olefins, allylic alcohols and their corresponding ester derivatives, allylic ethers, allylic halo compounds, allylic aryl compounds, vinyl amides, vinyl chlorides, vinylidene chlorides, and combinations thereof. Appeal Br. 17 (Claims App.). Thus, even if unexpected, the results of the Specification’s Examples 1-4 are not commensurate with the scope of the claims with respect to Appeal 2021-002184 Application 12/441,844 11 either the amount of dispersant used-because no results are shown for amounts near either the top or the bottom of the claimed range-or the type of dispersant used-because no dispersant other than a styrene/methacrylic acid copolymer is exemplified, and no basis is provided for expecting similar results for other copolymers within the scope of claim 9. See Kao, 639 F.3d at 1068 (“If an applicant demonstrates that an embodiment has an unexpected result and provides an adequate basis to support the conclusion that other embodiments falling within the claim will behave in the same manner, this will generally establish that the evidence is commensurate with [the] scope of the claims.”). DECISION SUMMARY In summary: Claim(s) Rejected 35 U.S.C. § Reference(s)/Basis Affirmed Reversed 9, 10, 14, 15, 23, 24, 26, 27, 30 103(a) Kirby, Crooks 9, 10, 14, 15, 23, 24, 26, 27, 30 TIME PERIOD FOR RESPONSE No time period for taking any subsequent action in connection with this appeal may be extended under 37 C.F.R. § 1.136(a). See 37 C.F.R. § 1.136(a)(1)(iv) (2019). AFFIRMED