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 .
Response to Amendment
The new grounds of rejection set forth below are necessitated by applicant’s amendment filed on September 18, 2025. In particular, claim 1 has been amended to recite the amounts (ppm) of the germanium and the tin in the catalytic system. This combination of limitations was not present at the time of the previous office action. Thus, the following action is properly made final.
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 and 4 is 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.
Regarding claim 1, this claim recites the limitation "total mass of the polymer" in the newly added amendment (twice). There is insufficient antecedent basis for this limitation in the claim. The examiner suggests replacing “polymer” with polyester”.
Regarding claim 4, the limitation “most preferentially” renders the claim indefinite because it does not clearly indicate whether the limitations that follow are mandatorily present. The examiner suggests deleting the phrase and the species that follow the phrase.
Claim Objections
Claim 5 is objected to because of the following informalities: if the transitional phrase “selected from” is used, please insert the word “or” between the limitations of the first stage and the second stage for clarity. Appropriate correction 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, 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) 1-7, 9-10 and 12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Yoon et al (Synthesis and Characteristics of a Biobased High Tg Terpolymer, Macromolecules, 2013, vol 46, pages 7219-7231) in view of Crawford et al (US 2006/0287496).
Regarding claims 1-4, 9 and 12, Yoon teaches a method of manufacturing a polyester comprising:
Terephthalic acid, ethylene glycol, 1,4 cyclohexane dimethanol and isosorbide are introduced into a reactor (page 7220, experimental section)
Adding in a germanium and tin catalyst (page 7220, experimental section)
Polymerizing the monomers to form the polyester
Recovering the polyester composition comprising the polyester and the catalytic system (page 7220).
Yoon teaches that the catalysts are germanium oxide and dibutyl tin oxide (page 7220, experimental section), however fails to teach that the element germanium is present in the amount of 180 to 220 ppm relative to the total mass of the polyester and the element tin is from 75 to 125 ppm relative to the total mass of the polyester.
Crawford teaches a polyester synthesis (Abstract) which incorporates tin and geranium catalysts in the amounts which range from 10 to 250 ppm ([0132]).
It would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to use the tin and geranium catalysts of Yoon in the amounts as taught by Crawford. One would have been motivated to do so based on the type of metal in the catalyst and based on the weight of the final polymer (Crawford, [0132]).
Regarding claim 5, Yoon teaches that there is a first stage in which the reaction medium is stirred at a temperature of 255 C to form oligomers and then at 270 C to form the polyester (page 7220, experimental section).
Regarding claim 6, Yoon teaches that the catalytic system is introduced prior to the polymerization step (page 7220, experimental section).
Regarding claim 7, modified Yoon does not teach the ratio of Ge:Sn in the claimed amount. However, it is well known in the art to optimize result effective variables such as catalyst amounts as noted by Crawford (adjusting the catalyst amounts based on the type of metal and the weight of the final polymer, [0132]). See MPEP 2144.05. It would have been obvious to a person having ordinary skill in the art at the time of the invention to have optimized the ratio of the two catalyst, and the motivation to so would have been, as Crawford suggests, to adjust the catalyst amounts based on the type of metal and the weight of the final polymer, ([0132]).
Regarding claim 10, Yoon teaches that the polymerization occurs under inert nitrogen atmosphere (page 7220, experimental).
Claim(s) 1-7 and 9-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Brandenburg et al (US 2003/0204029) in view of Crawford et al (US 2006/0287496).
Regarding claims 1, 9 and 12, Brandenburg teaches a method for manufacturing a polyester comprising
A step of introducing, into a reactor, at least one diacid monomer ([0020)] and an isosorbide monomer ([0023], dianhydrohexitol) into a reactor ([0056])
A step of introducing into the reactor a catalytic system a catalyst comprising geranium and/or tin ([0056]- [0057])
A step of polymerizing said monomers to form the polyester ([0056])
A step or recovering a polyester composition comprising the polyester and the catalytic system (Examples).
However, Brandenburg fails to teach that the element germanium is present in the amount of 180 to 220 ppm relative to the total mass of the polyester and the element tin is from 75 to 125 ppm relative to the total mass of the polyester.
Crawford teaches a polyester synthesis (Abstract) which incorporates tin and geranium catalysts in the amounts which range from 10 to 250 ppm ([0132]).
It would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to use the tin and geranium catalysts of Brandenburg in the amounts as taught by Crawford. One would have been motivated to do so based on the type of metal in the catalyst and based on the weight of the final polymer (Crawford, [0132]).
Regarding claim 2-3, Brandenburg teaches that monomer A can be terephthalic acid, isophthalic acid, etc. ([0020]).
Regarding claim 4, Brandenburg teaches that the diol can be 1,4 – cyclohexane dimethanol ([0029]).
Regarding claim 5, Brandenburg teaches that there is a first stage where the mixture is heated to 230 C to 300 C ([0056]). The first stage in polymerization necessarily forms oligomers. It is noted that the second stage is not mandatorily present.
Regarding claim 6, as the polymerization cannot occur without the catalyst, the catalyst is necessarily added prior to the polymerization step.
Regarding claim 7, modified Brandenburg does not teach the ratio of Ge:Sn in the claimed amount. However, it is well known in the art to optimize result effective variables such as catalyst amounts as noted by Crawford (adjusting the catalyst amounts based on the type of metal and the weight of the final polymer, [0132]). See MPEP 2144.05. It would have been obvious to a person having ordinary skill in the art at the time of the invention to have optimized the ratio of the two catalysts, and the motivation to so would have been, as Crawford suggests, to adjust the catalyst amounts based on the type of metal and the weight of the final polymer, ([0132]).
Regarding claim 10, Brandenburg teaches that the polymerization step is done under inert atmosphere such as nitrogen (Examples).
Regarding claim 11, Brandenburg teaches that the 45 to 50 mole percent of the diacid component ([0026]).
Claim(s) 8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Brandenburg et al (US 2003/0204029) in view of Crawford et al (US 2006/0287496) and Rosenfeld (US 4,959,445).
The discussion regarding Brandenburg and Crawford in paragraph 8 above is incorporated here by reference.
Regarding claim 8, Brandenburg teaches that pigments can be added to the polyester ([0078]), however, fails to teach that there is a cobalt pigment present in the reaction mixture.
Rosenfeld teaches the addition of a cobalt pigment to the reaction system of a polyester compound (Abstract).
It would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to add the cobalt pigment of Rosenfeld to the reaction mixture as taught by Brandenburg. One would have been motivated to do so in order to receive the expected benefit of imparting a blue tint to the polyester (Rosenfeld, Abstract).
Claim(s) 1-12 is/are rejected under 35 U.S.C. 103 as being unpatentable over Jacquel et al (US 2017/0335055) in view of Oyasato et al (US 2003/0069354).
Regarding claims 1, 7, 9 and 12, Jacquel teaches a method for manufacturing a polyester comprising
A step of introducing, into a reactor, at least one diacid monomer and an isosorbide monomer (dianhydrohexitol) into a reactor ([0012])
A step of introducing into the reactor a catalytic system a catalyst comprising germanium ([0013])
A step of polymerizing said monomers to form the polyester ([0014])
A step or recovering a polyester composition comprising the polyester and the catalytic system ([0015]).
Jacquel teaches that the germanium catalyst is paired with an aluminum catalyst ([0063]), rather than the recited tin catalyst. It also fails to teach the recited amounts of the germanium and tin catalysts.
Oyasato teaches a polymerization process which can use catalysts such as aluminum and tin catalysts ([0051]).
It would have been obvious to a person of ordinary skill in the art before the effective filing date of the claimed invention to replace the aluminum catalyst of Jacquel with the tin catalyst as taught by Oyasato. One would have been motivated to do so in order to receive the expected benefit of using a more reactive catalyst ([0051]).
Regarding the amounts of each of the catalysts, modified Jacquel then teaches that the total mass of the metal in the catalytic system ranges from 50 to 500 ppm of the total mass of the polymer obtained (Jacquel, [0080]). And the ratio between the germanium: tin ranges from 0.05:1 to 500:1 (Jacquel, [0070]). Therefore, the amounts of the germanium and the tin can be calculated to fall within the claimed range.
Regarding claim 2-3, Jacquel teaches that monomer is an aromatic monomer such as terephthalic acid ([0023]).
Regarding claim 4, Jacquel teaches that the monomer further comprise a diol such as ethylene glycol ([0034]).
Regarding claim 5, Jacquel teaches that the polymerization step comprises: a first stage during which the reaction medium is stirred at a temperature ranging from 220-310 C to form oligomers ([0084]) and a second stage during which the oligomers formed are stirred under vacuum at a temperature ranging from 240 to 330 C to form the polyester ([0085]).
Regarding claim 6, Jacquel teaches that the catalytic system is added before the polymerization step ([0081]).
Regarding claim 8, Jacquel teaches that the reaction mixture includes elemental cobalt as a pigment ([0077]).
Regarding claim 10, Jacquel teaches that there is a reaction deoxygenation step prior to the monomer polymerization step ([0093]).
Regarding claim 11, Jacquel teaches that the molar percentage of monomer (A) with respect to the total number of moles of monomers (A) and (B) is from 25-50% ([0041]).
Response to Arguments
Most of the 35 USC 112 issues that were cited in paragraph 8 of the office action mailed on May 21, 2025 have been addressed. One issue remains in claim 4 and that rejection is set forth above. All the other 35 USC 112 rejections are withdrawn.
Applicant's arguments filed September 18, 2025 have been fully considered but they are not persuasive for the reasons set forth below:
Applicant’s argument: There is no teaching or suggestion in Yoon, Brandenburg and Rosenfeld that the mass of the element geranium is from 180 to 220 ppm and the mass of the tin is from 75 to 125 ppm.
Examiner’s response: The newly presented limitations in the amendment filed on September 18, 2025 are addressed above with newly presented prior art references: Crawford, Jacquel, and Oyasato.
Conclusion
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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to DORIS L LEE whose telephone number is (571)270-3872. The examiner can normally be reached M-F 8 am - 5 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Arrie Lanee Reuther can be reached at 571-270-7026. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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DORIS L. LEE
Primary Examiner
Art Unit 1764
/DORIS L LEE/Primary Examiner, Art Unit 1764