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 .
Response to Amendment
The Amendment filed 01/08/2026 has been entered. Applicant’s amendments are in response to in the Non-Final Office Action mailed 09/08/2025. Applicant’s claims have been amended in the following manner: independent claim 1 has been narrowed to a formula much closer in nature with the previously elected species (see claim interpretation below for elected species). Other minor modifications and claim cancellations are made to the claim set.
Thus, the 103 rejection has been slightly modified to better focus on the narrowed scope of the new chemical formula of claim 1, but relies on the same basic rejection as previously stated. Furthermore, the Examiner points to different portions of Stern to better explain the original rejection (mainly, with regard to the selection and justification of compound species found in Table 2 of Stern, where the compound species of Table 2 were discussed as lead compounds in the previous Office Action, as explained below in the response to arguments), which does not constitute a new ground of rejection (i.e., the thrust of the previous Office Action is maintained - MPEP 1207.03(a)(II)(1)).
The following objections/rejections are withdrawn: the 112(b) rejection and the 103 rejection (based on Derian only, due to the narrowing of the chemical formula of claim 1).
The Examiner further acknowledges the following:
Claims 1, 3-4, and 10-15 are pending.
Claims 14-15 are withdrawn from consideration as directed to non-elected inventions.
Claims 1, 3-4, and 10-13 are presented for examination and rejected as set forth below.
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 1, 3-4, and 10-13 are rejected under 35 U.S.C. 103 as being unpatentable over Stern (WO2009082675A1 ; cited on the IDS filed 10/31/2022), and in further view of Noiret (Journal of Surfactants and Detergents, 1999).
Applicant’s claims are directed to a composition comprising an agrochemical and at least one surfactant of any of the chemical formula of instant independent claim 1. Note that claim 10 invokes product-by-process interpretations (i.e., in claim 10, the method of making a surfactant (the structure of which is finitely defined in claim 1) using specific reactants does not impact the structure of the final surfactant as defined in the instant formula, but it must be remembered: "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985). Although claim 10 recites the term “derivative”, the amount of derivatization is finite and definite as limited by the claimed R group definition and the claimed surfactant definition of claim 1.
Applicant elects the following species, where the species election is maintained:
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Where claim 1 is narrowed to further align with the elected species above (as reproduced below):
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Stern teaches a composition comprising an agricultural adjuvant amidoamine alkoxylate (abstract).
Regarding claims 1-4, and 11-13: Stern teaches an agricultural adjuvant amidoamine alkoxylate (abstract) characterized as a surfactant [0039]. Stern teaches the example below [0022], as representative of Examples (pg 7-8 and pg 15, table 2) that demonstrate the ability to make highly concentrated potassium glyphosate solutions that are bioefficacious [0036-0040], where x = 0-5 [0022]:
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This structure applies to the general formulas (Stern – claim 1):
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Note that the basic formulas of Stern teach modifications to obtain functional surfactants and overlap with the instant formulas. The formulas teach structures incorporating the mono amide functionality of instant formula I (instant claims 1 and 8) except there is a hydrogen or ethoxylate (up to 10 units, as depicted in the formula above for “b”), instead of a glyceryl (or polyglyceryl) substituent on the central nitrogen (Stern – claim 1). The formulas teach structures incorporating the bis amide functionality of instant formula II (instant claims 1 and 9) except there is a hydrogen or ethoxylate, instead of a glyceryl (or polyglyceryl) substituent on the central nitrogen (Stern – claim 1).
The interchangeability of the R, c, and a groups in Stern’s formula demonstrate an acceptable variability that allows the core structure to maintain surfactant functionality due to the similarity of substituents. Prior art structures do not have to be true homologs or isomers to render structurally similar compounds prima facie obvious. In re Payne, 606 F.2d 303, 203 USPQ 245 (CCPA 1979) (Claimed and prior art compounds were both directed to heterocyclic carbamoyloximino compounds having pesticidal activity. The only structural difference between the claimed and prior art compounds was that the ring structures of the claimed compounds had two carbon atoms between two sulfur atoms whereas the prior art ring structures had either one or three carbon atoms between two sulfur atoms. The court held that although the prior art compounds were not true homologs or isomers of the claimed compounds, the similarity between the chemical structures and properties is sufficiently close that one of ordinary skill in the art would have been motivated to make the claimed compounds in searching for new pesticides.).
Furthermore, with respect to the narrowed chemical formula of claim 1, the Examiner points Table 2 (i.e., discussed in the previous Office Action [“Stern teaches an amidoamine-based surfactant (Table 2 and [0021-0022]) from canola oil (which is known to contain C18 and C20 fatty acid derivatives) and diethylenetriamine (DETA), that can be modified according to the general chemical formulas of Stern (Stern – claim 1).”] ), which encompasses Example 15 formulation [0044] that makes use of Example 12 adjuvant [0041]:
The canola oil represents R1 in Stern’s formula, by contributing C18 amide functionality.
Diethylenetriamine represents the triamine core.
Ethoxylate is appended to the aminoamide core in [0041], according to the example structure.
Example 12 demonstrates a 48.7 wt% K-glyphosate formulation, incorporating only 8 wt% surfactant in formulation 15 [0044].
Thus, one could at once envision the core structure of the narrowed chemical formula of claim 1 (except for the polyglyceryl substitution). The only major difference between Stern and the narrowed chemical formula of instant claim 1 is the ethoxylate vs polyglyceryl substituent difference, which is addressed below through the teachings and motivations of Noiret.
Furthermore, Stern demonstrates compatibility of adjuvants of this structure with high concentration formulations of glyphosate solutions [0036-0039]. On pg 9 in Example 4, Stern demonstrates a Stern also teaches a method of making the compositions (Stern – claim 11) and a method of application (Stern – claim 18). Finally, Stern teaches that in certain embodiments, the nitrogen can be quaternized or can be an amine oxide, including variations of this type of substitution (reading on instant formulas (III-VI) [0013].
Regarding claim 7: In this case, the sources of the R hydrocarbon group does not affect the structural make-up of the R group as defined by the instant formulas claimed. The claim invokes a product-by-process interpretation, and note "[E]ven though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process." In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985).
In summary, Stern teaches amidoamine ethoxylates, where the amidoamine cores are the same basic cores of the instantly claimed compound formulas. Applicant is directed back to the structural example of Stern (above) that is used to make highly concentrated potassium glyphosate solutions, and the structural formula variations (also above) that Stern teaches that stem from this structure, as claimed variants (which overlap with instant formulas (I-VI), as discussed above). However, Stern does not teach the polyglyceryl substitution (but instead ethoxylate substituents) (instant claims 1-4), nor glycidol as a reactant to make polyglycerylamines (instant claim 10). Thus, the only major difference between Stern and the instant claim formula is the ethoxylate vs polyglyceryl difference on the core structure, which is addressed below through Noiret.
Noiret teaches that polyglyceryl is an acceptable substitution for ethoxylates (pg 345, paragraph 3) (such as the ethoxylates disclosed in Stern’s formulas), providing some improvement over ethoxylates such as being milder, safer, efficient, and safer for the environment in cosmetics (pg 349, paragraph 1-2). Noiret teaches glycidol as a reactant in the presence of an amine to make polyglycerylamines (reads on instant claim 10, in combination with the teachings of Stern) (pg 350, “synthesis of DGA”). The number of glyceryl units in the polyglyceryl moiety impact the final properties of surface tension and critical micelle concentration (abstract), and the number of glyceryl units that can be added are not limited in concept by the specific examples of the disclosure such as compound 7 (where at least two glyceryl units are linked in succession to the amine, that reads on instant claims 2-4):
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It would have been prima facie obvious for one of ordinary skill in the art before the effective filing date of the claimed invention to modify the ethoxylate substitution of the surfactant formulas in Stern’s disclosure with the polyglyceryl teachings of Noiret because Stern teaches an adjuvant that advantageously allows for high concentration formulations of glyphosate solutions, and Noiret teaches substituting ethoxylates with polyglycerol moieties provides improvement of the final surfactants such as being milder, safer, efficient, and safer for the environment in cosmetics (pg 349, paragraph 1-2).
Thus, Stern modified by Noiret teaches the obviousness of the species elected by the Applicant. Stern teaches an amidoamine-based surfactant (Table 2 and [0021-0022]) from canola oil (which is known to contain C18 and C20 fatty acid derivatives) and diethylenetriamine (DETA), that can be modified according to the general chemical formulas of Stern (Stern – claim 1). Substitution of the ethoxylates (up to 10 monomeric units in the formula) of Stern for polyglyercyl as motivated by Noiret would make obvious the elected species (as depicted at the beginning of this action), in further view of the chemical formulas taught by Stern (Stern – claim 1).
Response to Arguments
Applicants arguments, see pg 6-15, filed 01/08/2026, with respect to the 103 rejection of claims 1-8 and 10 (based on Derian) under rejection have been fully considered and are persuasive. Therefore, this 103 rejection has been withdrawn.
However, with respect to the 103 rejection of claims 1-13 (based on Stern, in view of Noiret) have been fully considered but they are not persuasive. The 103 rejection has been modified with respect to amendments made to the claim set. The thrust of the rejection remains the same as before, relying on the same references.
On page 6-7, Applicant summarizes a position before going into more detail. The edits made regarding the 112(b) rejection are found acceptable, and that rejection is withdrawn.
On page 7, Applicant argues (first) no reasonable expectation of success by modifying Stern with Noiret. With regard to reasonable expectation of success: “Applicants are reminded that obviousness does not require absolute predictability. See In re Rinehart, 531 F.2d 1048, 189 USPQ 143 (CCPA 1976) (indicating that evidence showing there was no reasonable expectation of success may support a conclusion of nonobviousness).” Noiret provides distinct motivation to substitute amino ethoxylated surfactants with polyglyceryl units (i.e., the polyglyceryl substituent is functionally equivalent to the ethoxylate substituent), providing additional benefits regard toxicity, stability, and environmental safety (pg 349). Furthermore, Noiret directly claims that “polyglyceryl surfactants are expected to be valuable substitutes for ethoxylates” (pg 354, paragraph 3). While Applicant comments on a general concern where Stern comments that “some alkoxylate adjuvants” are not suitable for high concentration formulations, absolute predictability of a modification is not required. It is routine in the Art to optimize chemical surfactant activity based on minor structural modifications (which is exemplified by the specific example highlighted in the arguments for tallowamine alkoxylate). Finally, Applicant has not provided evidence that the specific proposed modification of the obviousness rejection (i.e., the polyglyceryl for ethoxylate substitution) is inappropriate.
On page 7-8, Applicant argues (second) that it is not chemically possible to modify the amidoamine intermediate of Stern with polyglycerol because Stern teaches modification of amidoamine by appending ethoxylates. This rationale falls short because it does not consider the elements taught by Noiret. Noiret teaches polyglyceration of amines. A PHOSITA would understand that the generally chemistry to polyglycerate amines taught by Noiret would also apply to Stern’s intermediates (where in Stern’s general formula that is reproduced in the 103 rejection, the free nitrogens are substituted as H and/or ethoxylate). In an obviousness analysis, it is the combined teachings that are relevant.
Also, evidence has not been presented that calls into question the presumption of operability of the prior art. It should be remembered: “Affidavits or declarations attacking the operability of a patent cited as a reference must rebut the presumption of operability by a preponderance of the evidence. In re Sasse, 629 F.2d 675, 207 USPQ 107 (CCPA 1980). Further, since in a patent it is presumed that a process if used by one skilled in the art will produce the product or result described therein, such presumption is not overcome by a mere showing that it is possible to operate within the disclosure without obtaining the alleged product. In re Weber, 405 F.2d 1403, 160 USPQ 549 (CCPA 1969).” In this case, there is no evidence that the modification is not feasible, when Noiret shows polyglyceration of amines as chemically possible by example (pg 351, reaction figures).
On page 9-12, Applicant states there was a failure of Lead Compound Analysis. The Examiner points to text in the previous 103 rejection (of the previous Office Action) that points to “Table 2: Viscosity Measurements for selected Examples” (i.e., selected examples within a publication would be selected and motivated for optimization by a PHOSITA):
“Thus, Stern modified by Noiret teaches the obviousness of the species elected by the Applicant. Stern teaches an amidoamine-based surfactant (Table 2 and [0021-0022]) from canola oil (which is known to contain C18 and C20 fatty acid derivatives) and diethylenetriamine (DETA), that can be modified according to the general chemical formulas of Stern (Stern – claim 1). Substitution of the ethoxylates (up to 10 monomeric units in the formula) of Stern for polyglyercyl as motivated by Noiret would make obvious the elected species (as depicted at the beginning of this action), in further view of the chemical formulas taught by Stern (Stern – claim 1).”
In addition to Table 2 providing “selected Examples" of the disclosure, in a further pointing to text regarding the canola-based adjuvants (i.e., Examples 15 and 16 are described as fluid liquids [0044]) of Table 2 (as discussed in the previous Office Action shown above) as lead compounds, it would be apparent a PHOSITA that the canola-based adjuvants of Examples 15 and 16 produce low viscosity formulations [0044], which is a beneficial property of high concentrations glyphosate formulations [0026]. This is sufficient motivation to select why adjuvant 12 (which is used as the adjuvant in the high concentration potassium glyphosate (fluid liquid) formulations of Examples 15 and 16), would be selected as a lead for further development and modification.
On page 13-14, Applicant argues against Derian. The 103 rejection based on Derian is withdrawn due to Applicant’s narrowing of claim 1.
On page 14, Applicant claims superior and unexpected results (specifically, Sample 5 and Examples 2.7 and 2.8). Applicant demonstrates, in Example 2.7, a 39.6 K-glyphosate formulation, incorporating 8.7 % surfactant, that further requires APA-7 (alkyl-amidopropyl amine of C7 fatty acid, which structurally similar to Stern’s amidopropyl amines of fatty acids, and thus, likely has a surfactant/solubilizing effect). Stern demonstrates, in Example 15, a 48.7 wt% K-glyphosate formulation, incorporating only 8 wt% surfactant.
Objectively, Stern is able to achieve higher concentration formulation loadings (48.7 wt%) compared to the instant examples (39.6 wt%), such that the resulting performance of the instant Example formulations are expected (i.e., when Stern is modified by the polyglyceryl for ethoxylate substitution taught by Noiret, where Noiret teaches functional equivalence between ethoxylate and polyglyceryl amino substitution for surfactants). Noiret also teaches that polyglyceryl is an acceptable substitution for ethoxylates (pg 345, paragraph 3) (such as the ethoxylates disclosed in Stern’s formulas), providing some improvement over ethoxylates such as being milder, safer, efficient, and safer for the environment in cosmetics (pg 349, paragraph 1-2), and directly claims that “polyglyceryl surfactants are expected to be valuable substitutes for ethoxylates” (pg 354, paragraph 3).
Note that any differences between the claimed invention and the prior art may be expected to result in some differences in properties. The issue is whether the properties differ to such an extent that the difference is really unexpected. In re Merck & Co., 800 F.2d 1091, 231 USPQ 375 (Fed. Cir. 1986). Consequently, we must determine whether the results obtained in the closest prior art and those set forth by Applicants are sufficiently different in kind, and not merely in degree, so as to be unexpected by a person of ordinary skill in the art at the time of invention. See Iron Grip Barbell Co. v. USA Sports, Inc., 392 F.3d 1317, 1322 (Fed. Cir. 2004) (Unexpected results that are probative of nonobviousness are those that are "different in kind and not merely in degree from the results of the prior art") (citation omitted). In this case the Art shows comparable surfactant efficacy and teaches functional equivalence of the proposed modification of the obviousness rejection, rendering Applicant’s results for Examples 2.7 and 2.8 (as suitable surfactants for high concentration K-glyphosate formulations), as expected.
On page 15, Applicant requests rejoinder. However, the claims still stand under rejection.
Correspondence
THIS ACTION IS MADE FINAL. 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 extension fee 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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/R.P./Examiner, Art Unit 1614 2/4/2026
/SEAN M BASQUILL/Primary Examiner, Art Unit 1614