DETAILED ACTION
Claims 1-17 are currently pending in the instant application.
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 .
Election/Restrictions
Applicant’s election without traverse of species
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in the reply filed on 12/22/2025 is acknowledged.
Priority
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Information Disclosure Statement
Applicant's Information Disclosure Statements filed on 03/17/2023, 07/1/2023, 01/02/2024 and 12/09/2024 have been considered. Please refer to Applicant's copies of the 1449 submitted herewith.
Claim Objections
Claims 1-17 are objected to because of the following informalities: Claim 1 states in the 3rd line that “in the presence of one or more solvents selected from (B) (B1) an organic solvent [hereinafter referred to as component (B1)]”. The recitation (B)(B1) is unclear because it has two variables listed together without defining variable (B). As claims 2-17 do not clarify the issue, they have been included herein. To overcome the objection, examiner suggests amending the to “in the presence of one or more (B) solvents selected from [[ (B1) an organic solvent [hereinafter referred to as component (B1)]…” or similar, as presented in the instant specification (e.g. page 4, first full paragraph). Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claim 15 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 15 recites the limitation "content of the component (D)" in the 2nd line of the claim. There is insufficient antecedent basis for this limitation in the claim as claim 15 depends directly from claim 1 and there is no component D recited in claim 1.
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.
Claims 1-10 and 12-17 are rejected under 35 U.S.C. 103 as being unpatentable over BITTNER (see US Pub No. 2018/0201885, pub. 07/19/2018, cited in IDS filed 03/17/2023).
BITTNER teaches 150 g (0.387 mol) of maleic acid di(2-propylheptyl)ester and fumaric acid di(2-propylheptyl)ester, 190 g (0.473 mol) of methoxy-2-propanoland ammonium hydrogen sulfite are combined to give di (2-propylheptyl) sulfosuccinate ammonium salt - see paragraph [0670], p. 26. From this is obtained 220 g of solution, containing 62.5 wt % of desired compound, 37.2 wt % of methoxy-2-propanol and 0.3 wt % of water. Thus the mass ratio of (B1)/(S + B1 + B2) = 0.625 and (B1)/(S + B1 + B2) = 0.003. This reads on instant claim 1 except that the mass ratio of (B1)/(S + B1 + B2) is 0.003 rather than 0.03 or more.
Regarding the limitations of component (B2) found in claims 1 and 4, according to MPEP 2144.05, Section I, similarly, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. Titanium Metals Corp. of America v. Banner, 778 F.2d 775, 783, 227 USPQ 773, 779 (Fed. Cir. 1985) (Court held as proper a rejection of a claim directed to an alloy of "having 0.8% nickel, 0.3% molybdenum, up to 0.1% iron, balance titanium" as obvious over a reference disclosing alloys of 0.75% nickel, 0.25% molybdenum, balance titanium and 0.94% nickel, 0.31% molybdenum, balance titanium. "The proportions are so close that prima facie one skilled in the art would have expected them to have the same properties."). Further, MPEP 2144.05 Section II, Part A states that generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955) (Claimed process which was performed at a temperature between 40°C and 80°C and an acid concentration between 25% and 70% was held to be prima facie obvious over a reference process which differed from the claims only in that the reference process was performed at a temperature of 100°C and an acid concentration of 10%.); see also Peterson, 315 F.3d at 1330, 65 USPQ2d at 1382 ("The normal desire of scientists or artisans to improve upon what is already generally known provides the motivation to determine where in a disclosed set of percentage ranges is the optimum combination of percentages."); In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969).
Regarding claim 7, BITTNER teaches removal of insoluble salts to obtain 220 g of a solution. The solution contained 62.5 wt.-% of the desired compound, 37.2 wt.-% of methoxy-2-propanol and 0.3 wt.-% of water with the yield of desired structure was 91 mol % (with respect to theoretical amount of desired surfactant structures - some loss of material due to filtration and removal of insoluble salt). Thus, the insoluble salt is presumed to refer to the ammonium hydrogen sulfite and its hydrolyzed product. The ratio of component (C) to component (A) is 1.2 and the reaction occurs at 105 ºC. Further, BITTNER teaches metal ion content was <10 ppm and the insoluble component is removed through filtration.
Regarding claims 12-14, the BITTNER teaches that organic solvent compound may be selected from alcohols having a total number of 1 to 8 carbon atoms (more preferred 3 to 6 carbon atoms), alkyl ethylene glycol, alkyldiethylene glycol, alkyltriethylene glycol, alkylpropylene glycol, alkyl dipropylene glycol and alkyl tripropylene glycol (see paragraph [0280]-[0289], p. 10). Thus, though the reaction is exemplified with methoxy-2-propanol, BITTNER teaches said reaction may occur with multiple alcohol solvents. When a person of ordinary skill is faced with “a finite number of identified, predictable solutions” to a problem and pursues “the known options within his or her technical grasp,” the resulting discovery “is likely the product not of innovation but of ordinary skill and common sense.” KSR, 127 S. Ct. at 1742. So too, “[g]ranting patent protection to advances that would occur in the ordinary course without real innovation retards progress.” Id. at 1741.
Claim 1 and 11 are rejected over BITTNER (see US Pub No. 2018/0201885, pub. 07/19/2018, cited in IDS filed 03/17/2023) and MEYER (see US Pub No. 2007/0214999, pub. 09/20/2004, cited in IDS filed 03/17/2023) and Feustel (see US Pat. No. 5,908,582, issued 06/01/1999, cited in IDS filed 03/17/2023).
The limitations of claim 1 are taught as discussed above. MEYER teaches di-(2-propylheptyl)-maleate (produced in accordance with Example 2), 40 g of a solution of (a) 70% di-(2-propylheptyl)-sulfosuccinate, (b) 20% water and (c) 10% ethanol (note—the solution of the three components (a), (b) and (c) is obtained as the product of the described synthesis of Example 3. When Example 3 was carried out for the first time, the mixture of components (a), (b) and (c) was not yet available—40.0 g Hydropalat 875 were used instead), 142 g (0.75 mol) sodium disulfite and 194 g deionized water were introduced into a 1-liter four-necked flask equipped with a mechanical stirrer, heating system, reflux condenser and nitrogen inlet and were heated under reflux at 104° C. in a gentle stream of nitrogen until a clear solution was obtained (ca. 3 hours). After stirring for 10 minutes, no more sulfite could be detected in the product. On cooling, the product gelled/solidified which could be avoided by addition of a co-solvent: to this end, 50 g ethanol was added at ca. 80° C. – see Example 3, paragraph [0039], p. 3. Thus MEYER exemplifies preparation of a sulfonate by reacting component (A) - di-(2-propylheptyl)-maleate in the presence of component (C) di-(2-propylheptyl)-sulfosuccinate. Feustel teaches it can be of advantage to carry out the sulfitation reaction of the maleic acid diester in the presence of a surfactant, preferably the sulfosuccinic acid diester salt to be produced, as initiator. The reaction is easier to control from outset because otherwise it only starts after a certain time as a result of autocatalysis (see col. 4 lines 40-46).
Prior to the filing of the instant application, a PHOSITA following the teachings of MEYER and Feustel would have found it prima facie obvious to carry out the reaction of BITTNER using sulfosuccinic acid diester salt as initiator since Feustel teaches the advantage of using sulfosuccinic acid diester salt to help carry out the sulfitation reaction while MEYER exemplifies the process.
Claims 1-17 are rejected under 35 U.S.C. 103 as being unpatentable over Feustel (see US Pat. No. 5,908,582, issued 06/01/1999, cited in IDS filed 03/17/2023) teaches reacting a maleic acid diester corresponding to the formula ROOC--CH═CH--COOR', where R and R' independently of one another represent aliphatic or cycloaliphatic C3-22 alkyl, C2-22 alkenyl or optionally C1-8 -alkyl-substituted C6-22 aryl, with a sulfiting agent in the presence, in water as solvent and a co-solvent, characterized in that the co-solvent is a polymer containing alkylene oxide units at a temperature in the range of from about 60 to about 150° C with molar ratio of maleic acid diester to sulfiting agent, based on HSO3- is from about 1:09 to about 1:2. Further, 0.1 to about 20% by weight of the sulfosuccinic acid diester produced by the process is added to the reaction mixture in step I) as a reaction initiator – see claim 13-16. Feustel exemplifies said reaction with 295.5 g di-2-ethylhexyl maleate, 85.5 g of sodium disulfite powder, 190.1 g water, 35 g of 1,2-propylene glycol (see Example 1b, col. 5) to obtain 70% active substance content. This would correspond to 295.5 g/(340.5 g/mol) = 0.87 mol di-2-ethylhexyl maleate * 0.7 yield (70% active substance content) = 0.61 mol di-2-ethylhexyl sulfosuccinate * (580.56 g/mol) = 352.7 g di-2-ethylhexyl sulfosuccinate, which corresponds to (S) of the instant claims. The reaction mixture is cooled to room temperature and a clear, homogeneous liquid product of around 70% is obtained. Since no liquids are said to be removed from the closed reaction system and a clear, homogeneous liquid product having the active substance content is obtained, it is presumed based on the reaction amounts the amount of water and propylene glycol remains the same. Thus, the mass ratio of (B1)/(S + B1 + B2) =190.1/(350.7 + 190.1 + 35) = 0.33 and (B1)/(S + B1 + B2) = 35/(350.7 + 190.1 + 35) = 0.06. Further it states that the reaction mixture is stirred until it is free from sulfite (see Example 1, col. 5).
Regarding claim 2, Feustel exemplifies the process with compounds having R and R’ as 2-ethylhexyl rather than 2-propylheptyl. However, according to MPEP 2144.09, Section II states that compounds which homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious); Aventis Pharma Deutschland v. Lupin Ltd., 499 F.3d 1293, 84 USPQ2d 1197 (Fed. Cir. 2007) (5(S) stereoisomer of ramipril obvious over prior art mixture of stereoisomers of ramipril.).
Correspondence
Any inquiry concerning this communication or earlier communications from the examiner should be directed to KAREN CHENG whose telephone number is (703)756-4699. The examiner can normally be reached M-F, 9AM-6PM PST.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Adam Milligan can be reached at 571-270-7674. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/KAREN CHENG/Primary Examiner, Art Unit 1623
/ADAM C MILLIGAN/Supervisory Patent Examiner, Art Unit 1623