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 . Claims included in the prosecution are claims 1-17, 20 and 22-25.
Applicants' arguments, filed 09/08/2026, 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 Rejections and/or objections not reiterated from previous office actions are hereby withdrawn.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 Rejections - 35 USC § 112(b)
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.
Claims 1-17, 20 and 22-25 are 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.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, claims 1 and 25 recites the broad recitation a sum of contents of the compounds represented by Formula (8) to (10) is less than 31 ppm, and the claim also recites a content of the compound represented by Formula (B) is less than 8 ppm which is the narrower statement of the range/limitation. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. If a compound represented by Formula (B) is present, it is unclear whether the content is less than 8 ppm or less than 31 ppm.
Claim Rejections - 35 USC § 112(d)
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claims 2, 3, 5-7 and 20 are rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claims 2, 3, 5-7 and 20 fail to further limit the subject matter of claim 1 since each of these claims recite an amount of the compound of Formula (A) and/or the compound of Formula (B) that exceeds the less than 8 ppm limit for each of the compound of Formula (A) and the compound of Formula (B) recited in claim 1.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
Response to Arguments
Applicant argues that claim 1 does not require each of the compound of Formula (A) and the compound of Formula (B) to have a content of less than 8 ppm.
The Examiner does not find Applicant’s argument to be persuasive. The claims do not require the other compound to be present. Thus, the claims are not necessarily further limiting. For example, claim 2 recites a sum of the contents of the compounds represented by Formula (A) to be less than 66 ppm. The claim does not require a compound represented by Formula (B) to be present. If a compound represented by Formula (B) is not present, the claim is not further limiting claim 1.
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 1-17, 20, 22 and 25 are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Khandurina et al., (WO 2018/183628 A1, Oct. 04, 2018) (hereinafter Khandurina).
Khandurina teaches in the background that 1,3-BG (which also can be referred to as 1,3- butylene glycol) can be petro-BG, which is produced in a chemical process from petroleum derived acetylene via its hydration ([0004]). Khandurina discloses a bioderived 1,3-BG that is cosmetic grade (Claim 10). The bioderived 1,3-BG has a chemical purity of 99.9% or more ([0010]). The term "bioderived" means produced from or synthesized by a biological organism ([0087]). The bioderived 1,3-BG has overall lower levels of "heavies" and "lights" contaminants than petro-BG ([00134]). The term "lights" refers to compounds in a 1,3-BG sample that elute at earlier retention times than 1,3-BG, e.g., in a GC-MS chromatogram or an LC-MS chromatogram ([0090]). The term "heavies" refers to compounds in a 1,3-BG sample that elute at later retention times than 1,3-BG, e.g., in a GC-MS chromatogram or an LC-MS chromatogram ([0091]). The following exemplary compounds are believed to be present at a level of less than 1 ppm: acetaldehyde, 3-buten-2-one (methyl vinyl ketone), diacetyl, 2-butenal (crotonaldehyde), 3-hydroxy-2-butanone (acetoin), or combinations thereof ([00153]). The bioderived 1,3-BG may have nondetectable or less than 10 ppm of 3-hydroxy-butanal (i.e., acetaldol) and 4-hydroxy-2-butanone (i.e., 1-hydroxy-3-butanone) ([00154] and [00155]). The bioderived 1,3-BG may also contain acetone as a contaminant (Table 11).
Accordingly, Khandurina anticipates the instant claims insofar as disclosing a bioderived 1,3-butylene glycol having a chemical purity of 99.9% or more ([0010]), wherein the contaminants include methyl vinyl ketone, 4-hydroxy-2-butanone (i.e., 1-hydroxy-3-butanone, acetone, crotonaldehyde, 3-hydroxy-butanal (i.e., acetaldol), and acetaldehyde ([00153]-[00155] and Table 11). As noted in the instant specification on page 18, last paragraph, methyl vinyl ketone, 1-hydroxy-3-butanone, acetone, formaldehyde, crotonaldehyde, acetaldol, and acetaldehyde are precursors of the compounds represented by Formula (A) or (B). As noted in the specification in paragraph [0197], when the initial contents of acetaldehyde, crotonaldehyde, methyl vinyl ketone, acetone, formaldehyde, butylaldehyde, acetaldol, and 1-hydroxy-3-butanone were low, impurities represented by Formulas (1) to (10) did not increase so much or did not increase at all. Therefore, since the bioderived 1,3-butylene glycol of Khandurina may comprise an amount of the precursors that form the compounds represented by Formula (A) and/or (B), the bioderived 1,3-butylene glycol of Khandurina comprises an amount of the compounds of Formula (A) and/or (B). Additionally, since the bioderived 1,3-butylene glycol of Khandurina has a chemical purity of 99.9% or more and the amount of contaminants in the bioderived 1,3-butylene glycol of Khandurina may be less than 1 ppm, the compounds represented by Formula (A) and/or (B) formed from the contaminants would be less than 1 ppm as well.
In regards to instant claims 1 and 25 reciting keeping 1,3-butylene glycol at 180°C for 3 hours, this is merely a product-by-process limitation. Even 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. See MPEP 2113. As discussed above, Khandurina teaches a 1,3-buytlene glycol product having less than 1 ppm of contaminants, which meets the instant claims. Therefore, the claim is unpatentable even though the prior product was made by a different process.
Regarding claim 4, since Khandurina teaches substantially the same precursors of the compounds represented by Formulas (A) and/or (B), the bioderived 1,3-butylene glycol of Khandurina necessarily has substantially the same compounds of Formulas (A) and/or (B).
Regarding claims 11-13, since Khandurina teaches substantially the same1,3- butylene glycol product as claimed, the 1,3-butylene glycol product of Khandurina has substantially the same properties as the 1,3-butylene glycol product claimed.
Regarding claim 14, as noted in the instant specification in paragraph [0010], acetic acid is an impurity of an acetaldol. As discussed above, Khandurina teaches less than 10 ppm acetaldol. Therefore, the 1,3-butylene glycol product of Khandurina has less than 16 ppm acetic acid.
Regarding claim 22, the claim is a product-by-process claim. Even 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. See MPEP 2113. In the instant case, as discussed above, Khandurina discloses a bioderived 1,3-butylene glycol produced from or synthesized by a biological organism, which is substantially the same as the product claimed. Therefore, the claim is unpatentable even though the prior product was made by a different process.
Response to Arguments
Applicant argues that the amounts of the compounds generated upon heating are not necessarily determined solely by the initial amounts of their alleged precursors.
The Examiner does not find Applicant’s argument to be persuasive. As noted in the instant specification on page 18, last paragraph, methyl vinyl ketone, 1-hydroxy-3-butanone, acetone, formaldehyde, crotonaldehyde, acetaldol, and acetaldehyde are precursors of the compounds represented by Formula (A) or (B). Therefore, since the bioderived 1,3-butylene glycol of Khandurina may comprise an amount of the precursors that form the compounds represented by Formula (A) and/or (B), the bioderived 1,3-butylene glycol of Khandurina may comprise an amount of the compounds of Formula (A) and/or (B). Khandurina discloses wherein the 1,3-butylene glycol has a chemical purity of 99.9% or more. Thus, the claimed amount of a compound represented by Formula (A) and a compound represented by Formula (B) would have been obvious since it is within the purity range taught by Khandurina. Applicant has not shown wherein the 1,3-butylene glycol cannot have an amount of a compound represented by Formula (A) and a compound represented by Formula (B) within the claimed range. As, such, Applicant’s argument is unpersuasive.
Applicant argues that the natural result flowing from the method as taught in Khandurina would not result in the claimed 1,3-butylene glycol product.
The Examiner does not find Applicant’s argument to be persuasive. Applicant has not explained why the method taught in Khandurina would not result in the claimed 1,3-butylene glycol product. Although Khandurina discloses a different method than what is disclosed in the instant specification, Applicant has not shown wherein the method disclosed in the instant specification is the only method able to arrive at the claimed product. As such, Applicant’s argument is unpersuasive.
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 23 and 24 are rejected under 35 U.S.C. 103 as being unpatentable over Khandurina et al., (WO 2018/183628 A1, Oct. 04, 2018) (hereinafter Khandurina) in view of Interchimie (Butylene glycol, July 2019).
The teachings of Khandurina are discussed above. Khandurina does not teach wherein the 1,3-butylene glycol comprises formaldehyde.
However, Interchimie discloses wherein the material data sheet for 1,3 butylene glycol (page 1), which states that the presence of formaldehyde is technically unavoidable (page 2).
Accordingly, it would have been prima facie obvious to one of ordinary skill that the 1,3-butylene glycol comprises formaldehyde since presence of formaldehyde is technically unavoidable as taught by Interchimie.
Regarding the amount of formaldehyde recited in claim 24, since the bioderived 1,3-butylene glycol of Khandurina has a chemical purity of 99.9% or more, it would have been obvious that that amount of formaldehyde present may be less than 47 ppm.
Conclusion
Claims 1-17, 20 and 22-25 are rejected.
No claims are 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 nonprovisional extension fee (37 CFR 1.17(a)) 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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/TRACY LIU/Primary Examiner, Art Unit 1614
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