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 .
DETAILED ACTION
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on April 14, 2026 has been entered.
Claims 1 and 4-13 are pending.
Claims 2 and 3 are cancelled.
Claims 1 and 5 are currently amended.
Claims 12 and 13 are new.
Claims 5-11 remain withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention, there being no allowable generic or linking claim.
Claims 1, 4, 12 and 13 as filed on April 14, 2026 are under consideration.
Withdrawn Objections / Rejections
In view of the amendment of the claims, all previous claim rejections under 35 USC 102(a)(1) by Hartmann are withdrawn.
Applicant’s arguments have been fully considered. Rejections and/or objections not reiterated from previous office actions are hereby withdrawn. The following rejections and/or objections are either reiterated or newly applied. They constitute the complete set presently being applied to the instant application.
Claim Objections
Claim 1 is objected to because of the following informalities: “in a form of an aqueous solution” should presumably recite “in aqueous solution” or some variation thereof because this clause is drawn to the active ingredient. Appropriate correction / clarification is required.
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 of this title, 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 set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
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.
Claims 1, 4, 12 and 13 are rejected under 35 U.S.C. 103 as being unpatentable over Hartmann (DE 4,300,320 A1, published July 14, 1994, as evidenced by the USPTO machine translation, of record) as evidenced by Niehaus et al. “Identification of a metabolic disposal route for the oncometabolite S-(2-succino)cysteine in Bacillus subtilis,” Journal of Biological Chemistry 293(21):8255-8263, 2018, of record, and optionally in view of Chilcote Chilcote (US 2,581,514, published January 8, 1952, of record).
Hartmann teaches a composition comprising a mercaptan (thiol) compound inclusive of cysteamine for reducing hair keratin and comprising fumaric/maleic acid and/or salts (title; abstract; claims). Part of the mercaptan reducing agent is bound to the double bond of maleic acid / fumaric acid (forms a composite) (page 3):
PNG
media_image1.png
156
752
media_image1.png
Greyscale
The composition is intended for permanent waving of the hair (e.g., title), as required by instant claim 4.
Hartmann teaches successively adding thio groups to the double bond of maleic acid or fumaric acid increases the mildness of the preparation on the hair (reduces the reducing power) (page 4, 3rd full paragraphs).
Hartmann exemplifies an embodiment comprising a reducing agent solution 1a comprising 27.0 g aqueous ammonium thioglycolate solution, 50% and an aqueous solution 1b comprising 4.0 g maleic acid (pages 4-5; claims). Hartmann further teaches the two solutions 1a and 1b are mixed in volume ratios of 9:1 to 2:8 (claim 8; also, Table on page 5 of original document).
Regarding the product-by-process limitations as required by instant claims 1 and 12 drawn to reacting 1 mole of the amino thiol with 0.8 to 1.2 moles of the organic acid salt and drawn to reacting approximately equimolar proportions, product-by-process claims are not limited to the manipulations of the recited steps, only the structure implied by the steps. See MPEP 2113. In the instant case Hartmann illustrates an embodiment of a reaction product comprising 2 thiols and 1 dicarboxylic acid. However, Hartmann further teaches the degree of reaction of the thiol with the dicarboxylic acid correlates with the mildness of the preparation on the hair and as such it would have been prima facie obvious to optimize the degree of reaction (e.g., ratios less than 2 thiols per dicarboxylic acid) in order to attain the desired mildness on the hair. It is prima facie obvious to optimize such result-effective variables within prior art conditions or through routine experimentation. See MPEP 2144.05 II. Additionally or/and alternatively, the exemplary embodiment comprises about 0.12 moles thiol (~= (27 g * 0.50) / (109.15 g/mole)) and about 0.03 moles maleic acid (~= 4.0 g / 116.07 g/mole), wherein the two compositions may be mixed (reacted) in ratios of 9:1 to 2:8. When the exemplary compositions are mixed at a ratio of 2:8, the reaction occurs at a reactant ratio of about 1:1.
Additionally, Niehaus evidences thiols such as cysteine spontaneously and readily react with fumarate resulting in the formation of stable S-(2-succino)-adducts according to the following mechanism (abstract; Figure 1):
PNG
media_image2.png
492
860
media_image2.png
Greyscale
suggesting the cartoon of Hartmann reproduced supra is mechanistically incorrect and that the reaction product of Hartmann comprises at most one C-S bond.
Alternatively, Chilcote teaches production of thiasuccinic acid derivatives using water as the reaction medium for the interaction of a saturated non-tertiary hydrocarbon thiol with maleate ions:
PNG
media_image3.png
224
266
media_image3.png
Greyscale
wherein the reaction is conducted at temperatures of about 25 to 150 ºC (title; column 1, lines 9-26; column 2, lines 28-36; column 3, lines 51-58; claims). One mole of alkali metal maleate in solution in water reacts with one mole of an immiscible saturated alkyl non-tertiary hydrocarbon thiol (paragraph bridging columns 1 and 2), as required by instant claim 12. The molar ratio of thiol to maleate salt charged to the reaction zone can be varied from about 1 (equimolar) to 10, preferably about 1 to 2 (column 2, lines 24-27), as required by instant claim 12.
It would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to modify the two solutions of Hartmann, the first comprising a mercaptan (thiol) compound inclusive of cysteamine and the second comprising fumaric/maleic acid/or salts thereof, such that the molar ratio of the mercaptan (thiol) to the fumaric/maleic acid/or salts thereof charged to the reaction zone (when mixed together) varies from about 1 to 10, preferably about 1 to 2 as taught by Chilcote because this molar ratio is suitable for producing thiolated derivates of maleate thereby removing the free mercaptan (thiol) from solution. See MPEP 2144.05 for information regarding numerical ranges.
Regarding claim 13 which recites a reducing power of 0.02 mL or less, because Hartmann or/and Hartmann in view of Chilcote render obvious aqueous solutions of the composites as instantly claimed, prepared according to the process as instantly claimed, the composites of Hartmann or/and of modified Hartmann necessarily have a reducing power, as determined using an iodometry method (as defined in paragraph [0032] of the instant specification), of 0.02 mL or less because a chemical composition and its properties are inseparable. See MPEP 2112. In further support of this presumption, Examples 1 and 2 of the instant specification evidence a reducing powder of 0.02 mL or less is a property of the products produced when cysteamine is reacted either with fumaric acid or with maleic acid (e.g., paragraphs [0054]-[0057], Table 1 at page 21).
Response to Arguments: Claim Rejections - 35 USC § 103
Applicant’s arguments have been fully considered but they are not persuasive.
Applicant’s repeated argument at pages 4-5 of the Remarks that the Applicant’s product is not the same product as disclosed by Hartmann remains unpersuasive for reasons of record. Additionally, the instant claims embrace any / all composites. Applicant’s citation to the cartoon of Hartmann as not encompassing a reaction carried out at a molar ratio of 1:0.8 to 1.2 remains unpersuasive because there is a difference between carrying out the process of a reaction and the reaction product per se. Nonetheless, the rejection over Hartmann has been modified to incorporate the evidence of record that the cartoon of Hartmann is mechanistically incorrect and to articulate a new rationale for the modification of the reaction process of Hartmann to operate within the molar ratios newly claimed. See also Khatik as newly cited infra drawn to thia-Micheal addition chemistry.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Khatik et al. “Catalyst-free conjugation addition of thiols to a,b-unsaturated carbonyl compounds in water,” Organic Letters 8(11):2433-2436, 2006 teaches water activates the a,b-unsaturated carbonyl and the thiol in thia-Michael addition in the creation of a single C-S bond across a double bond (title; abstract).
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ALISSA PROSSER whose telephone number is (571)272-5164. The examiner can normally be reached M - Th, 10 am - 6 pm.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, DAVID BLANCHARD can be reached on (571)272-0827. 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.
/ALISSA PROSSER/Examiner, Art Unit 1619
/BENNETT M CELSA/Primary Examiner, Art Unit 1600
Prosecution Insights