DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-20 are pending as filed on 11/21/2024.
Information Disclosure Statement
The information disclosure statement filed 11/21/2024 includes items of information that fail to comply with the requirements of 37 CFR 1.98.
37 CFR 1.98(a)(3)(i) requires a concise explanation of the relevance, as it is presently understood by the individual designated in 37 CFR 1.56(c) most knowledgeable about the content of the information, of each reference listed that is not in the English language. This has not been provided for Foreign Patent Document 5 (JP 45-19281), and therefore the reference has not been considered.
37 CFR 1.98(b)(5) requires that each publication listed must be identified by publisher, author (if any)... date and place of publication. The required identifiers have not been provided for Non-patent literature document 4, and it is not clear what kind of document or publication Applicant has provided. Therefore, the item of information has not been considered.
Priority
Applicant’s claim for the benefit of a prior-filed application under 35 U.S.C. 119(e) or under 35 U.S.C. 120, 121, 365(c), or 386(c) is acknowledged. Applicant has not complied with one or more conditions for receiving the benefit of an earlier filing date under 35 U.S.C. 119(e) or under 35 U.S.C. 120 or 121 as follows:
The later-filed application must be an application for a patent for an invention which is also disclosed in the prior application (the parent or original nonprovisional application or provisional application). The disclosure of the invention in the parent application and in the later-filed application must be sufficient to comply with the requirements of 35 U.S.C. 112(a) or the first paragraph of pre-AIA 35 U.S.C. 112, except for the best mode requirement. See Transco Products, Inc. v. Performance Contracting, Inc., 38 F.3d 551, 32 USPQ2d 1077 (Fed. Cir. 1994).
The disclosures of the prior-filed applications, Application Nos. 62/199918, 15/223178, 16/739733 and 17/727147, fail to provide adequate support or enablement in the manner provided by 35 U.S.C. 112(a) or pre-AIA 35 U.S.C. 112, first paragraph for one or more claims of this application.
Claim 1 of the instant application limits the content of tetrahydrofuran (THF) and/or methyl tert-butyl ether in the propiolactone (PPL) composition to an amount greater than 0 ppm to 100 ppm.
Provisional application 62/199918 recites a composition comprising less than 10 ppm THF (see [0018], claims 200, 247). However, there is no disclosure of a range THF which includes values higher than 10 ppm, and therefore, no support for a range of greater than 0 to 100 ppm as recited in claim 1. The provisional application further names methyl tert-butyl ether as a solvent [0222], but nowhere describes a range of greater than 0 to 100 ppm methyl tert-butyl ether in a PPL composition. For at least the reason that there is no support for the amount of tetrahydrofuran and/or methyl tert-butyl ether recited in claim 1, claims 1-20 are not entitled to the benefit of 62/199918.
The claims of prior filed application 15/223178 recite less than 500 ppm of tetrahydrofuran (see e.g., claim 42). However, none of the prior filed applications describe a PPL composition comprising greater than 0 to 100 ppm methyl tert-butyl ether. For at least the reason that there is no support for the amount of methyl tert-butyl ether recited in claim 1, claims 1-20 are not entitled to the benefit of any of Application Nos. 62/199918, 15/223178, 16/739733 and 17/727147. Therefore, the presently claimed invention can only rely on the filing date of the instant application, which is 11/21/2024.
Additionally, there is no support in any prior filed application for at least the following dependent claims:
Claim 6: there is no description in a prior filed application of a PPL composition having an acrylic acid or acrylic acid dimer concentration as presently recited.
Claim 18: there is no description in a prior filed application of a PPL composition having a butylated hydroxy toluene concentration as presently recited.
Claim 19: there is no description in a prior filed application of a PPL composition having a 3-hydroxy propionic acid concentration as presently recited.
Claim 20: there is no description in a prior filed application of a PPL composition having a ppl oligomer concentration as presently recited.
Claim Objections
Claim 1 is objected to because of the following informalities: “ethery” should be “ether.” 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.
Claims 11-13, 16, 17 and 20 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.
Claims 11-13 and 16 depend from claim 1 (directly or indirectly) and refer to components which must be present in amounts within certain ranges. However, the referred to components (“the succinic anhydride,” “the acetaldehyde,” “the acetic acid”) are not previously recited and therefore lack antecedent basis, rendering the scope of the claims unclear. Applicant may wish to consider amending these claims to a format such as used in dependent claim 4.
Claim 17 also lacks antecedent basis because it refers to “the beta-propiolactone level” rather than simply “the beta-propiolactone.” The examiner recommends deletion of the word “level.”
Claim 20 further limits claim 1 by requiring “ppl oligomers” in an amount within a range of 0 to about 10 ppm. The abbreviation “ppl” has been interpreted as “polypropiolactone,” however, the abbreviation should be defined in the claim or replaced with the full name. More critically, claim 1 recites a composition which comprises at least 90 wt% “polypropiolactone” (i.e., “ppl”). Neither claim 20 nor the instant specification provides any indication as to how “ppl oligomers” should be distinguished from the general term “polypropiolactone” in claim 1. It is not clear, therefore, how one would determine whether a composition falls within the scope of claim 20, since it is not clear what molecular weights of polypropiolactone should be considered part of the 90 wt% of “polypropiolactone” required by claim 1, and what molecular weights of polypropiolactone are considered “ppl oligomers” and therefore limited to amounts within a range of 0 to 10 ppm.
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.
Claim 9 is 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.
The range recited in claim 9 (upper limit 500 ppm) is broader than the corresponding range recited in claim 1 (upper limit 100 ppm), and therefore, claim 9 fails to further limit 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.
Claim Rejections - 35 USC § 102
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.
Claim(s) 1-5, 7-10 and 14-17 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Sookraj et al (US 2022/0251018).
As to instant claims 1, 2, 4, 9, 17, Sookraj discloses (see claims 11 and 17) a composition wherein the ranges of each component fall within the corresponding ranges recited in the instant claims. The composition disclosed by Sookraj comprises:
polypropiolactone having a concentration of at least 95 wt%
cobalt or ions thereof in an amount of 10 ppm or less,
aluminum in an amount of 10 ppm or less,
beta-propiolactone in an amount of 10 ppm or less (claim 17),
tetrahydrofuran in an amount of 10 ppm or less.
As to claim 3, the presently recited range is recited in claim 12 of Sookraj.
The recitations of instant claims 5, 7 and 8 are recited in claims 5, 7 and 8 of Sookraj.
The ranges recited in instant claims 10 and 14 are met by the range recited in claim 14 of Sookraj.
The range recited in instant claim 15 is met by the range recited in claim 15 of Sookraj.
The range recited in instant claim 16 is taught in claim 1 of Sookraj.
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.
Claim(s) 1-17, 19 and 20 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sookraj et al (US 2017/0029352, herein “Sookraj-2”).
As to claims 1, 2, 4, 9-11, 16 and 17, Sookraj-2 recites (claim 42) a solid transportable composition comprising:
at least 95 wt% polypropiolactone (which falls within the presently claimed ranges in claims 1 and 2),
less than 1 ppm cobalt or ions thereof (within the presently claimed range),
less than 10 ppm β-propiolactone (within the presently claimed ranges in claims 1, 9 and 17),
less than 10 ppm of succinic anhydride (within the range in claim 11),
less than 10 ppm aluminum or ions thereof (within the range recited in claim 4),
less than 10 ppm acetic acid (within the range in claim 16), and
less than 500 ppm tetrahydrofuran (encompassing the presently claimed range).
Sookraj-2 discloses transporting “essentially pure, essentially dry solid post-purification PPL…” The composition is meant for transporting to a glacial acrylic acid (GAA) production process [0156]. The system is meant to achieve GAA with a purity of at least 99.9% [0090]. Considering Sookraj-2’s disclosure, the person having ordinary skill in the art would have been motivated to minimize the content of every component in the composition other than polypropiolactone (i.e., minimize the content of every impurity) in order to increase the purity of the ultimately desired GAA product. It would have been obvious to the person having ordinary skill in the art, therefore, to have decreased the content of every component in Sookraj-2’s polypropiolactone composition within the ranges disclosed by Sookraj-2, including decreasing the content of tetrahydrofuran to a value within the presently claimed range of greater than 0 to 100 ppm. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05.
As to claims 3, 14 and 15, the range of “at least 95 wt%” polypropiolactone disclosed by Sookraj-2 in claim 42 encompasses the presently claimed range of at least 98 wt%, and, Sookraj-2’s claim 42 ranges of less than 1 ppm cobalt and less than 10 ppm aluminum encompass the presently claimed range of greater than 0 to 100 ppb for each component. It would have been obvious to the person having ordinary skill in the art to have increased the content of polypropiolactone and decreased the content of each impurity to any concentration within Sookraj-2’s disclosed range in order to increase the purity of the ultimately obtained GAA, including to a polypropiolactone concentration of at least 98 wt%, and to cobalt and aluminum contents of greater than 0 to 100 ppb. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05.
As to claims 5 and 8, Sookraj-2 discloses the recited molecular weight range in [0610] and the recited PDI in [0612].
As to claim 6, Sookraj-2 teaches that the ultimately obtained glacial acrylic acid has an acrylic acid dimer content of less than 200 ppm [0658]. However, Sookraj-2 fails to teach the content of acrylic acid or acrylic acid dimer in the solid polypropiolactone composition which is transported to the GAA production system. However, Sookraj-2 teaches transporting solid PPL to a GAA product stream [0632-3]. Given that formation of acrylic acid is not desired until the PPL is delivered to the GAA production system, and given Sookraj-2’s teaching to transport PPL which is “essentially pure, essentially dry solid post-purification PPL…” [0156], it would have been obvious to the person having ordinary skill in the art to have decreased the content of any impurity in Sookraj-2’s solid PPL, including acrylic acid or acrylic acid dimer, to any concentration, including to within the presently claimed range of greater than 0 to 100 ppm.
As to claim 7, Sookraj-2 discloses the recited formula in [0606] and content thereof in [0608].
As to claims 12 and 13, Sookraj-2 fails to disclose the concentration of acetaldehyde in the solid PPL composition. However, Sookraj-2 teaches isolating a β-propiolactone monomer product stream (which is later polymerized to form the PPL) which contains acetaldehyde in a mass fraction of 0.0005 to 0.001 [0120], and which is then purified to provide β-propiolactone which is essentially free of acetaldehyde [0123], [0408]. It would have been obvious to the person having ordinary skill in the art, therefore, to have purified β-propiolactone, as taught by Sookraj-2, in order to decrease the content of every undesired impurity and to provide β-propiolactone which is essentially free of acetaldehyde, including to an acetaldehyde content which results in an acetaldehyde content in the subsequently obtained PPL within the presently claimed ranges.
As to claim 19, Sookraj-2 fails to disclose the presently recited 3-HPA content in the PPL composition. Sookraj-2 exemplifies a process wherein the content of 3-HPA in crude PPL is reduced after washing [0671]. There is reasonable basis to conclude, therefore, that Sookraj-2 discloses PPL which has at least some 3-HPA (i.e., greater than 0 ppm). Considering that Sookraj-2 discloses a process which reduces the content of 3-HPA and generally desires essentially pure PPL for transport as a solid material, it would have been obvious to the person having ordinary skill in the art to have purified Sookraj-2’s PPL to achieve any desired low 3-HPA content in order to increase the purity of PPL and the ultimately obtained GAA, including to a content within the presently claimed range of greater than 0 ppm to about 10 ppm.
As to claim 20, Sookraj-2 fails to disclose the presently recited ppl oligomer content in the composition. However, Sookraj-2 discloses various ranges for “n” in the PPL [0609], and ranges of suitable molecular weights [0610]. Sookraj-2 further teaches a PDI of less than 2.0 [0612]. Considering that Sookraj-2’s disclosed PDI ranges have no lower limit, one having ordinary skill in the art would have been motivated to decrease the PDI of Sookraj-2’s PPL in order to achieve any appropriately narrow molecular weight distribution within Sookraj-2’s disclosed range. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed PPL having any appropriately high molecular weight within the ranges taught by Sookraj-2 in [00609-10] and to have selected any appropriately low PDI within Sookraj-2’s disclosed range of less than 2.0, including a molecular weight and PDI which corresponds to a content of “ppl oligomers” within the presently claimed range. Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05.
Claim(s) 18 is/are rejected under 35 U.S.C. 103 as being unpatentable over Sookraj et al (US 2022/0251018).
The rejection under 35 USC 102(a)(1) over Sookraj is incorporated here by reference.
Sookraj fails to teach a butylated hydroxy toluene (BHT) concentration of greater than 0 to 10 ppm.
However, Sookraj teaches that the systems disclosed include various purification systems to produce GAA of high purity, and that the systems are configured to achieve a purity of at least 99.9% [0079]. Sookraj discloses utilizing a THF solvent recovery distillation column for removal of BHT inhibitor from make-up THF [0425]. The distillate stream consists of essentially pure THF having a purity greater than 99.9 wt% [0427].
Considering Sookraj’s desire for a GAA of at least 99.9% purity and Sookraj’s further teaching of a system for removing BHT from THF and achieving THF having a purity of 99.9 wt%, the person having ordinary skill in the art would have been motivated to reduce the content of any impurity which would contaminate the desired GAA end product to any appropriately low concentration in order to improve the quality of the GAA. It would have been obvious to the person having ordinary skill in the art, therefore, to have purified THF, as taught by Sookraj, to remove BHT to any appropriate extent, including to an extent which results in a polypropiolactone composition having a BHT concentration within the presently claimed range.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/RACHEL KAHN/Primary Examiner, Art Unit 1766
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