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
This Office action is responsive to Applicant's Remarks and Amendment after Non-Final Rejection, filed Oct. 06, 2025. As filed, Claims 1-4 are pending are pending of which claims 1-3 are amended. Claim 4 is withdrawn from consideration. Claim 5 is cancelled.
Response to Remarks
Applicant’s amendments have been fully considered and are entered. The status for each rejection and/or objection in the previous Office Action is set out below.
1.The rejection of claims 1-3 under 35 U.S.C. § 112 second paragraph is withdrawn per amendment to claims.
2.The rejection of claims 2-3 under 35 U.S.C. § 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph is withdrawn per amendment to claims.
3.The rejection of claims 1-3 under 35 U.S.C. § 102(a)(1) and 102(a)(2) over Patent 2,470,859, by Pavlic, 1949 is maintained. Applicants arguments have been carefully reviewed however these were not found persuasive for the following reasons.
The Applicants argue that the ordinary artisan would not have arrived at the current composition practicing the disclosure of Pavlic. Therefore, the reference does not teach every element as required by the claimed invention (Remarks page 6-8). The specification exemplify production of the 3,5,5- trimethylhexanoicacid by synthesizing 3,5,5-trimethylhexanal by a hydroformulation reaction of diisobutylene and oxo gas (carbon monoxide CO) with a subsequent oxidation step. The specification details in Comparative Example 1 that the current composition is made by the hydroformulation reaction of diisobutylene and oxo gas (CO) with a subsequent oxidation step and a distillation. Pavlic discloses the preparation of the current composition by synthesizing 3,5,5-trimethylhexanal by a hydroformulation reaction of diisobutylene and oxo gas (carbon monoxide CO) with a subsequent oxidation step. Distillation steps are also included in the disclosure (see Example 1, columns 3-4 of Pavlic).
In response it is noted that the specification broadly allows for any and all synthetic methods to produce the current composition. Concerning the production of the 3,5,5-trimethylhexanoic acid composition, the specification recites “the method for producing a 3,5,5-trimethylhexanoic acid composition according to the embodiment is not particularly restricted”. This statement is being interpreted as being very broad and encompasses any method to prepare 3,5,5-trimethylhexanoic acid
Moreover, of 3,5,5-trimethylhexanoic acid can be reduced sufficiently by a conventional purification method such as distillation. In other words, distillation lowers the concentration of the t-butyl alcohol. As to applicants assertion that Pavlic does not disclose the current composition, it is noted that given that the specification does not particularly restricting the synthetic pathways to achieve the current composition and that conventional purification methods such as distillation reduce t-butyl alcohol sufficiently, the distillation and redistillation of Pavlic does just that.
Note: Example 1 of Pavlic, disclose a redistilled product –or a second distillation. The applicant has not offered evidence that the product of Pavlic is not the claimed composition. With the specification stating that “t-BuOH which is produced as a byproduct during the production of 3,5,5-trimethylhexanoic acid can be reduced sufficiently by a conventional purification method such as distillation”, and Pavlic performing an additional distillation, the claimed composition is therefore present in the disclosure of the prior art.
WO2022118917 performs a distillation, Pavlic redistills the distilled product and distillations sufficiently remove t-BuOH, as evidence by the original disclosure. Applicant has not supplied evidence to the contrary. The rejection is being maintained.
Applicant argues “Comparative Example 1 and Pavlic disclose substantially identical methods yielding substantially identical products. Regarding the production of the 3,5,5-trimethylhexanoic acid composition, the specification recites “the method for producing a 3,5,5-trimethylhexanoic acid composition according to the embodiment is not particularly restricted”.
The specification exemplify production of the 3,5,5-trimethylhexanoic acid by synthesizing 3,5,5-trimethylhexanal by a hydroformulation reaction of diisobutylene and oxo gas (carbon monoxide CO) with a subsequent oxidation step (paragraph 25).
The specification details in Comparative Example 1 that the current composition is made by the hydroformulation reaction of diisobutylene and oxo gas (carbon monoxide CO) with a subsequent oxidation step and a distillation.
Pavlic discloses the preparation of the current composition by synthesizing 3,5,5-
trimethylhexanal by a hydroformulation reaction of diisobutylene and oxo gas (carbon monoxide CO) with a subsequent oxidation step. Distillation steps are also included in the disclosure (see Example 1, columns 3-4 of Pavlic).
The ‘859 patent discloses the preparation of the composition by synthesizing 3,5,5-trimethylhexanal in solvents such as butanol by a hydroformylation reaction of diisobutylene and oxo gas (carbon monoxide CO) with a subsequent oxidation step. Distillation steps are also included in the disclosure (see Example 1, col 3-4).
Given that the prior art teaches a similar process, by same steps and materials to synthesize 3,5,5-trimethylhexanal to the process of preparation the claimed composition, the claimed composition 3,5,5-trimethylhexanoic acid and t-butyl alcohol would necessarily be formed in the process of the ’859 patent. As noted, instant disclosure discuss that the t-butyl alcohol is obtained as by-product in the hydroformylation/oxidation synthesis of 3,5,5-trimethylhexanoic acid.
In other words, since the process steps, reactants, reaction conditions for 3,5,5-trimethylhexanal are all present as discussed by the ‘859 patent and since the materials are all recited by prior art and the reaction conditions are proper, the t-butyl alcohol as recited in the claims would necessarily be present in composition with 3,5,5-trimethylhexanoic acid.
4.The rejection of claims 1-3 under 35 U.S.C. § 103 over Patent 2,470,859, by Pavlic, 1949 is maintained for the same reasons as outlined above.
5.The NSDP rejection of claims 1-3 over claim 1-3 of copending Application No. 18870240 is withdrawn per submission of terminal disclaimer.
Claim Rejections - 35 USC § 102
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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-3 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by US Patent 2,470,859, by Pavlic, 1949 (the ‘859, cited by Applicants in IDS).
Claims interpretation: Instant claims are drawn to a 3,5,5-trimethylhexanoic acid composition comprising 3,5,5-trimethylhexanoic acid and t-butyl alcohol.
The measurement of t-butyl alcohol concentration does not add structural limitations to the claimed composition and therefore does not further limit the claimed composition.
Regarding the limitation "concentration in terms of toluene-d8” this does not add structural features to the claimed composition.
Regarding the limitations :” concentrated sample is measured by”, “heating program”, these can be considered to be product-by-process limitation. MPEP 2113 recites ““[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).
Regarding the measurement conditions, these conditions do not add structural features to the claimed composition nor do the conditions further limit the claimed composition.
Claims 2-3 are composition claims with an intended use. The claimed use of composition as cosmetic product and refrigeration oil do not impart further structural limitations onto the claimed composition. Upon achieving the claimed composition, a cosmetic product and a refrigeration oil are met.
The claimed cosmetic product and refrigeration oil do not impart further structural
limitations onto the claimed composition.
The claimed composition is being interpreted to be made as a mixture comprising 3,5,5-trimethylhexanoic acid and t-butyl alcohol.
Note: Instant disclosure discusses that tert-butyl alcohol is produced as a byproduct during the production of 3,5,5-trimethylhexanoic acid can be reduced sufficiently by a conventional purification method such as distillation” and “it was found through gas chromatography-olfactometry with a higher sensitivity that a very small amount of t-butyl alcohol (t-BuOH) exists in a 3,5,5-trimethylhexanoic acid composition immediately after the production (page 6-9).
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Therefore, upon producing 3,5,5-trimethylhexanoic acid, the presence of t-BuOH concentrations as claimed are expected to be attained in the hydroformylation/oxidation synthesis of 3,5,5-trimethylhexanoic acid from the corresponding aldehyde.
The ‘859 patent discloses the preparation of the composition by synthesizing 3,5,5-trimethylhexanal in solvents such as butanol by a hydroformylation reaction of diisobutylene and oxo gas (carbon monoxide CO) with a subsequent oxidation step. Distillation steps are also included in the disclosure (see Example 1, col 3-4).
Given that the prior art teaches a similar process, by same steps and materials to synthesize 3,5,5-trimethylhexanal to the process of preparation the claimed composition, the claimed composition 3,5,5-trimethylhexanoic acid and t-butyl alcohol would necessarily be formed in the process of the ’859 patent. As noted, instant disclosure discuss that the t-butyl alcohol is obtained as by-product in the hydroformylation/oxidation synthesis of 3,5,5-trimethylhexanoic acid.
In other words, since the process steps, reactants, reaction conditions for 3,5,5-trimethylhexanal are all present as discussed by the ‘859 patent and since the materials are all recited by prior art and the reaction conditions are proper, the t-butyl alcohol as recited in the claims would necessarily be present in composition with 3,5,5-trimethylhexanoic acid.
Substantially identical methods yield substantially identical products. See MPEP 2112.01 I. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
Therefore, the prior art teaches the limitations of insta claims.
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 1-3 are rejected under 35 U.S.C. 103 as being unpatentable over US Patent 2,470,859, by Pavlic, 1949 (the ‘859, cited by Applicants in IDS).
Claims interpretation: Instant claims are drawn to a 3,5,5-trimethylhexanoic acid composition comprising 3,5,5-trimethylhexanoic acid and t-butyl alcohol.
The measurement of t-butyl alcohol concentration does not add structural limitations to the claimed composition and therefore does not further limit the claimed composition.
Regarding the limitation "concentration in terms of toluene-d8” this does not add structural features to the claimed composition.
Regarding the limitations :” concentrated sample is measured by”, “heating program”, these can be considered to be product-by-process limitation. MPEP 2113 recites ““[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).
Regarding the measurement conditions, these conditions do not add structural features to the claimed composition nor do the conditions further limit the claimed composition.
Claims 2-3 are composition claims with an intended use. The claimed use of composition as cosmetic product and refrigeration oil do not impart further structural limitations onto the claimed composition.
The claimed composition is being interpreted to be made as a mixture comprising 3,5,5-trimethylhexanoic acid and t-butyl alcohol.
Note: Instant disclosure discusses that tert-butyl alcohol is produced as a byproduct during the production of 3,5,5-trimethylhexanoic acid can be reduced sufficiently by a conventional purification method such as distillation” and “it was found through gas chromatography-olfactometry with a higher sensitivity that a very small amount of t-butyl alcohol (t-BuOH) exists in a 3,5,5-trimethylhexanoic acid composition immediately after the production (page 6-9).
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Therefore, upon producing 3,5,5-trimethylhexanoic acid, the presence of t-BuOH concentrations as claimed are expected to be attained.
The ‘859 patent discloses the preparation of the composition by synthesizing 3,5,5-trimethylhexanal in solvents such as butanol by a hydroformylation reaction of diisobutylene and oxo gas (carbon monoxide CO) with a subsequent oxidation step. Distillation steps are also included in the disclosure (see Example 1, col 3-4).
Given that the prior art teaches a similar process, by same steps and materials to synthesize 3,5,5-trimethylhexanal to the process of preparation the claimed composition, the claimed composition 3,5,5-trimethylhexanoic acid and t-butyl alcohol would necessarily be formed in the process of the’859 patent. As noted, instant disclosure discuss that the t-butyl alcohol is obtained as by-product in the hydroformylation/oxidation synthesis of 3,5,5-trimethylhexanoic acid.
In other words, since the process steps, reactants, reaction conditions for 3,5,5-trimethylhexanal are all present as discussed by the ‘859 patent and since the materials are all recited by prior art and the reaction conditions are proper, the t-butyl alcohol by-product as recited in the claims would necessarily be present in composition with 3,5,5-trimethylhexanoic acid.
Substantially identical methods yield substantially identical products. See MPEP 2112.01 I. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977). "When the PTO shows a sound basis for believing that the products of the applicant and the prior art are the same, the applicant has the burden of showing that they are not." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990).
One of ordinary skill in the art would have a reasonable expectation of success in obtaining the claimed composition of 3,5,5-trimethylhexanoic acid and t-butyl alcohol by-product/impurity (as discussed in the disclosure, t-butanol is expected to be formed as impurity) as the prior art teach production of 3,5,5-trimethylhexanoic acid by same process.
The rationale to support a conclusion that the claim would have been obvious is that teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention. KSR, 550 U.S. at_, 82 USPQ2d at 1395.
Thus, the claimed invention as a whole is prima facie obvious over the teachings of the prior art.
Conclusion
In view of the rejections to the pending claims set forth above, no claim is allowed.
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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 date of this final action.
Telephone Inquiry
Any inquiry concerning this communication or earlier communications from the
examiner should be directed to:
Ana Muresan
(571) 270-7587 (phone)
(571)270-8587 (fax)
Ana.Muresan@uspto.gov
The examiner can normally be reached Monday - Friday (9:00AM - 5:30PM).
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at 571-270-5241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ANA Z MURESAN/Primary Examiner, Art Unit 1692