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 1, 3-4 and 7-16 are currently pending. Claim 1 is independent.
Claimed Priority
The instant application claims priority as follows:
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Response to Election/Restriction
Applicant's election, without traverse, of Group I, claims 1, 3-4 and 7-16, drawn to a process for refining glycolide, in the reply filed on December 15, 2025 is acknowledged. Applicant did not elect one specific species of solvent A and one specific species solvent B as requested by the examiner. However, the examiner is hereby withdrawing the requirement for species election since the solvent species are patentably indistinct.
Claims 1, 3-4 and 7-16 have been examined and are the subject of this Office Action.
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 1, 3-4 and 7-16 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.
The amended claims recite “having the boiling point under atmospheric pressure of”. Here this term is ambiguous. It is unclear if this means at atmospheric pressure or below atmospheric pressure. Nowhere in this application or in the priority application a reduced pressure was discussed for said solvent limitation, thus, it looks like there is no support in this application for a pressure below atmospheric pressure. The priority document recites “under normal pressure” and “at normal pressure” interchangeably. Original claim 1 recites “at normal pressure”. Thus, it appears that the phrase means “at atmospheric pressure”. However, some of the claimed alcohol solvents in the specification and instant claim 12 have a higher boiling point at atmospheric pressure than that in claim 1. For example, pentanol boiling point at atmospheric pressure is 138°C, but claim 1 requires a boiling point of 120°C or lower.
Claim 3 recites “in step (1), solvent I and solvent II are added simultaneously”. However, step (1) is a step of extracting, and does not mention addition of a solvent and to what or where the solvent is added. There is no antecedent basis for that limitation in the claims.
Claim 8 is redundant. It repeats numerous limitations that are present in claim 1. This can be overcome by removing the redundant recitations. Claim 8 could recite: The process for refining glycolide according to claim 4, wherein solvent I is selected from polyalkylene glycol ethers and solvent II is selected from saturated monohydric alcohols.
In claim 9 it is unclear if the resulting filter cake at that is collected by filtering at step (2) is different from the separated out glycolide crystals.
Claim 9 recites a process and it also recites “
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” Due to the word “preferably”, the claim is considered indefinite because there is a question or doubt as to whether the feature introduced by such language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claim.
Claim 10 recites the limitation "the filter cake obtained". There is insufficient antecedent basis for this limitation in the claim.
Regarding claims 10 through 15, the phrase "for example" (and “e.g.”) renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d).
In claim 16, the word “preferably” and phrase “more preferably”, makes the claim indefinite because there is a question or doubt as to whether the feature introduced by such language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claim.
Claim 16 recites “the terminal carboxyl content”. There is no antecedent basis for that limitation in the claims.
Dependent claims are rejected for containing the same issues.
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 3-4 and 7-16 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.
Claim 3 does not further limit claim 1 since it only mentions all the possible options for adding solvent I and solvent II.
Claim 7 does not further limit claim 4 since it encompasses all the possible options for solvent B that may be present in claim 4.
Claim 12 recites alcohol solvents with a higher boiling point at atmospheric pressure than that required in claim 1. Thus, claim 12 does not further limit the subject matter of claim 1. For example, pentanol boiling point at atmospheric pressure is 138°C, but claim 1 requires a boiling point of 120°C or lower.
Claim 13 claims a scope that encompasses diethylene glycol diether, which has a boiling point of 162°C at atmospheric pressure. This does not further limit what is required 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.
Dependent claims are rejected for containing the same issues.
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.
Claim(s) 1, 3-4, 7-8, 10, 12-13 and 15-16 are rejected under 35 U.S.C. 103 as being unpatentable over US 2003/0191326, in view of US Patent 5,830,991, further in view of CN100999516 (cited by applicant) and CN107868075 (cited by applicant).
Recitations of examples or preferences in the claims have been taken as optional.
US2003/0191326 teaches how to remove the large molecular weight impurities in glycolide that are usually glycolic acid oligomers. It teaches purifying a crude cyclic ester by extraction of impurities from crude glycolide in which a co-distillation of glycolide in the presence of polyalkyleneglycol ether solvents (B) and a solubilizing agent (C) provides a glycolide containing phase (from distillate) and an impurity-containing phase (from initial mixture or mother liquor). The glycolide from the distillate is separated and recrystallized from ethyl acetate. Thus, recrystallization is directly carried out after step (1).
The crude glycolide was formed from depolymerization of glycolic acid oligomers. See particularly, examples 10-12, paragraphs [0036-0038], polyalkene glycol ethers (B) at para [0066], [0072], and suggested solubilizing agents (C) that include monohydric alcohols and aliphatic alcohols, such as decanol, tridecanol and decanediol at para [0087].
US 5,830,991 teaches the similar method from the above art with a solubilizing agent added since it is effective for dissolving tar residue, so the amount of tar is reduced. It additionally teaches at column 8:
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CN100999516 teaches a method for purifying glycolide by removing impurities, such as water, and for producing high yield and high purity glycolide by recrystallization in isopropanol or other alcohols, or in a mixture of alcohol and acetone. See the claims and examples.
CN107868075 teaches a method of coupling recrystallization and alcohol washing, which can make glycolic acid and glycolic acid dimer impurities in the purified glycolide low, and the yield and purity of glycolide refined are high. The recrystallization solvent is preferably at least one or more than two of ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, n-amyl alcohol, and isoamyl alcohol. The amount of the recrystallization solvent is preferably 0.5-3 times the mass of crude glycolide. See whole document.
Ascertainment of the Difference Between the Prior Art and the Claims
(MPEP §2141.012)
US2003/0191326 does not teach recrystallization in alcohol, such as isopropyl alcohol as claimed.
However, processes for refining glycolide by recrystallization as claimed in isopropanol and other alcohol solvents was common in the art. Additionally, CN107868075 teaches that their recrystallization in alcohols is better than recrystallization using ethyl acetate.
Finding of prima facie obviousness--rational and motivation (MPEP §2142-2413)
The primary references are in the same field of endeavor. One of ordinary skill in the art is a chemist practitioner with the knowledge and skill of the authors of the references cited to support the examiner's position.
The Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper "functional approach" to the determination of obviousness as laid down in Graham. See MPEP 2143.
Examples of rationales that may support a conclusion of obviousness include:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
(E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
(F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
(G) Some 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.
Applying KSR example rationale (G), it would have been prima facie obvious for a person having ordinary skill to combine the purification process of US2003/0191326 in which extraction of impurities from crude glycolide was performed by a co-distillation of glycolide in the presence of polyalkyleneglycol ether solvents (B) and a solubilizing agent (C), such as decanol, with the recrystallization steps of the glycolide containing phase in propanol solvent, as performed by CN100999516 or CN107868075. The advantages of the recrystallization in alcoholic solvents taught by CN100999516 and CN107868075 would have motivated the artisan to combine the processes with a reasonable expectation of success.
Regarding claim 10, at least the teachings of CN107868075 would achieve the limitation of step (2) since it taught that the amount of the recrystallization solvent is preferably 0.5-3 times the mass of crude glycolide.
Claim(s) 1, 3-4, 7-8 and 10-16 are rejected under 35 U.S.C. 103 as being unpatentable over JP2002128777A in view of CN100999516 and CN107868075, all cited by applicant.
Recitations of examples or preferences in the claims have been taken as optional.
JP2002128777A teaches a method for purifying glycolide, obtained by depolymerizing a glycolic acid oligomer in presence of polyalkylene glycol as depolymerization solvent, by washing with an alcohol. After polymerization, the formed glycolide is distilled off together with the depolymerization solvent, the distillate is cooled to 80° C or lower, the precipitated glycolide is separated by solid-liquid separation and the glycolide filter cake obtained contains depolymerization solvent, which is washed with an organic solvent, preferably an alcohol having 1 to 4 carbons, such as isopropyl alcohol (paragraphs [0016-0017]). Paragraph [0038] teaches that the precipitated glycolide is a crystalline substance, subjected to solid-liquid separation. After separation, the depolymerization solvent is still attached to the crystals in a filter cake state. The depolymerization solvent has a high boiling point and is difficult to remove by drying. Thus, for removing the depolymerization solvent, a method of washing and replacing with an organic solvent is performed. Para [0040] teaches that alcohols having a number of 1 to 4 are more preferable as organic solvents because they have a larger polarity and an excellent cleaning effect than alcohols having more carbon atoms. In particular, isopropyl alcohol is most preferable because it has low reactivity with glycolide and is less likely to produce a by-product. Para [0041] teaches that the number of times of washing can be 1 to 10 times as a batch operation, and a continuous washing method is also employed.
See particularly, Example 5: The depolymerization reaction was performed in the same manner as in Example 2 except that 50 g of polyethylene glycol monomethyl ether #350 (average molecular weight 350, manufactured by Aldrich) was used as the solubilizer. After the co-distillation was completed, the total amount of glycolide precipitated from the distillate was filtered off with a glass filter to obtain 36 g of a filter cake (according to GC analysis, it was 33 g of glycolide and 3 g of DEG-DB), 36 g of filter cake as mixed with 230 g of isopropyl alcohol (GL solubility (25° C.): 0.9%), stirred for 20 minutes, washed and replaced. After washing, it was filtered with a glass filter and vacuum dried at 30°C. After drying, the obtained purified glycolide was 32 g (yield: 80%), and the purity by GC (area method) was 99.99%, which was high purity. The amount of DEG-DB in the mother liquor and the reaction liquid was determined by GC to be 198 g (residual rate: 99%), and it was confirmed that there was almost no loss of solvent.
CN100999516 teaches a method for purifying glycolide by removing impurities, such as water, and for producing high yield and high purity glycolide by recrystallization in isopropanol or other alcohols or in a mixture of alcohol and acetone. See the claims and examples.
CN107868075 teaches a method of coupling recrystallization and alcohol washing, which can make glycolic acid and glycolic acid dimer impurities in the purified glycolide low, and the yield and purity of glycolide refined are high. The method comprises at least the following steps: (1) adding a recrystallization solvent to crude glycolide at room temperature; (2) Under the protection of an inert gas, heat and dissolve the mixture of crude glycolide and recrystallization solvent, and after hot filtration, lower the temperature of the filtrate at a stirring speed of 10-200rpm, and control the cooling rate at 0.1-1°C/min between; drop below 25°C to crystallize glycolide, remove the liquid phase by filtration, and dry the obtained solid to obtain recrystallized glycolide.
The recrystallization solvent is preferably at least one or more than two of ethanol, n-propanol, isopropanol, n-butanol, isobutanol, tert-butanol, n-amyl alcohol, and isoamyl alcohol. The amount of the recrystallization solvent is preferably 0.5-3 times the mass of crude glycolide. See whole document.
See for example, example 1: Mix 200g of product crude glycolide with 300g of n-propanol and heat to 80°C to form a homogeneous solution. After hot filtration, the filtrate was transferred to a three-neck flask, and cooled to room temperature at a rate of 0.5° C./min at a rotation speed of 100 rpm. Glycolide was precipitated from the system, and the glycolide crystals obtained after filtration were vacuum-dried at 70° C. for 5 hours to obtain 157 g of solids, with a yield of 79%, or example 2.
Ascertainment of the Difference Between the Prior Art and the Claims
(MPEP §2141.012)
The difference is that the primary reference did not further recrystallize glycolide after washing the filter cake containing the polyalkylene glycol ether with the alcohol.
However, processes for refining glycolide by recrystallization in isopropanol and other alcohol solvents was common in the art. See at least the secondary references.
Finding of prima facie obviousness
The Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper "functional approach" to the determination of obviousness as laid down in Graham. See MPEP 2143.
Examples of rationales that may support a conclusion of obviousness include:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
(E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
(F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
(G) Some 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.
Applying KSR example rationale (G), it would have been prima facie obvious for a person having ordinary skill to combine the purification process of JP2002128777A with the recrystallization steps of the glycolide containing phase in isopropanol solvent, as performed by CN100999516 or CN107868075. The advantages of the recrystallization in alcoholic solvents taught by CN100999516 and CN107868075 would have motivated the artisan to combine the two processes with a reasonable expectation of success.
Regarding claim 10, at least the teachings of CN107868075 would achieve the limitation of step (2) since it taught that the amount of the recrystallization solvent is preferably 0.5-3 times the mass of crude glycolide.
Regarding claim 11, the primary reference teaches 3 g of DEG-DB (solvent I) and 230g of isopropyl alcohol.
Conclusion
Claims 1, 3-4, 7-8 and 10-16 are rejected. No claim is allowable.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to VALERIE RODRIGUEZ-GARCIA whose telephone number is (571)270-5865. The examiner can normally be reached Monday-Friday 9:30am-5:30pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton Brooks can be reached at 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/VALERIE RODRIGUEZ-GARCIA/ Primary Examiner, Art Unit 1621