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
Claim Status
Claims 16-32 are pending. Claims 16-32 are under examination. Claims 16, 21-26 and 30-31 are rejected. Claims 18-20, 27-29 and 32 are objected to. No claims allowed.
Filing Receipt
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Claim Objections
Claim 16 and all dependent claims are objected to because of the following informalities: Claim 16, in line 3 recites “the first alcohol B”. This phrase is most likely referring to “a first alcohol” in line 2 of claim 16. However, the letter “B” in the phrase “the first alcohol B” may be referring to another “a first alcohol” or may include limitations not implicitly/explicitly disclosed in the claims. As to why the letter “B” was utilized adds ambiguity to the claims. Appropriate correction is required.
Claim 17 is directed to “the first alcohol”. Questions arise as to what the “first alcohol” in claim 17 is referring to. The “a first alcohol” in line 2 of claim 16 or the “the first alcohol B” in line 3 of claim 16.
Additionally, claims 18, 20, 24, 27, 28-29 and 31-32 explicitly recite the phrase “the first alcohol”. Moreover, none of the claims of record clarify what the “the first alcohol B” is. Thus all current claims are objected to.
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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claim(s) 16, 21-24, 26, and 30-31 is/are rejected under 35 U.S.C. 103 as being unpatentable over Zhao et al. (Recycling Polyurethanes through Transcarbamoylation, ACS Omega, 6 (6): pp. 4175–4183, Published 02-2021), and Bock et al. (US Patent 8,680,323, Patent date 03-2014).
Scope of the Prior Art
Bock et al. teach performing a thermolysis reaction on a carbamate, thereby obtaining an isocyanate and a product alcohol as a product and (d) separating the isocyanate of (c) from the product alcohol of (c).
For example, Bock et al. teach “The object is achieved by a process for preparing isocyanates by thermal dissociation of carbamates and separation by distillation of the reaction mixture from the carbamate dissociation, comprising the corresponding isocyanate and the corresponding alcohol, by distillation in a column having an enrichment section and a stripping section, where the carbamate is introduced between the enrichment section and the stripping section and the isocyanate is taken off as a constituent of the bottom stream and the alcohol is taken off as a constituent of the overhead stream from the column, in the presence of an inert solvent…” (column 2,
lines 1-25).
The above distillation is the current distillation in claim 23 and the above corresponding alcohol taught by Bock et al. is the product alcohol of claim 16 step (c).
Concerning the “a first alcohol” and presumably “the first alcohol B”, Bock et al. teach “Suitable alcohols for preparing the carbamates are in principle all aliphatic alcohols. Preference is given to selecting alcohols whose boiling points differ sufficiently from the boiling point of the isocyanates to ensure optimal separation. Particular preference is given to using aliphatic monohydroxy alcohols having from 1 to 4 carbon atoms per molecule, i.e. methanol, ethanol,…” (column 3, lines 25-40).
Bock et al. teach 4,4'-diisocyanatodiphenylmethane (MDI) (column 4, lines 15-25). Current claim 26.
Concerning claim 21 and 26 and the temperature of the thermolysis reaction, Bock et al. teach 210 to 400C (column 3, lines 15-20). This overlaps the current range in claim.
Concerning claim 30 and the inert gas, Bock et al. teach an inert solvent in the gaseous form (column 7, lines 5-10).
Ascertain the Differences
Bock et al. does not teach the current methods to obtain the carbamate in current steps (a) through (b).
Secondary References
Zhao et al. teach the methanolysis of polyurethane using t-BuOK and THF to yield a dimethylcarbamate 2a (see immediately below) (p. 4177-8). The methanolysis is the current step (a). Zhao et al. teach 2a was isolated using silica column chromatography hexanes/EtOAc (p. 4177-8). The isolation is current step (b).
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Concerning obtaining an isocyanate in current step (c) from the first carbamate and the recycling of polyurethane, Zhao et al. teach “Alternatively to this route, the O-dimethylcarbamate 2a can be isolated due to its stability and possibly converted subsequently into MDI44,45 offering new perspectives to regenerate diisocyanates to feed back into the classical PU industry” (bridging columns page 4180) and teach “Alternatively, each constituent resulting from depolymerization can be isolated, particularly the O-dimethylcarbamates which due to their stability can be further reacted to synthesize new PUs (nonisocyanate routes)49 or converted to diisocyanates to be fed back into the classical PU industry to generate virgin PUs (p.4182).
Concerning claim 22 and at least two polyurethanes, Zhao et al. teach different possible MDI derivatives (isomers, polymeric forms)… (p. bridging pp. 4180-4181).
Concerning claim 24, Zhao et al. teach methanolysis is performed at 55 or 65C.
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have prepared 4,4'-diisocyanatodiphenylmethane (MDI) as taught by Bock et al. via the thermal dissociation of the corresponding carbamate, and isolating MDI and the corresponding alcohol, by distillation with a reasonable expectation of success. The ordinary artisan would have done so because of the teachings of Bock et al. Wherein MDI, and methanol were explicitly taught. Upon doing so the ordinary artisan would have arrived at steps (c) and (d) of claim 16.
The ordinary artisan would have then looked to the teachings of Zhao et al. to satisfy a source of the carbamate that can be made into the MDI. The ordinary artisan would have done so because Zhao et al. teach the O-dimethylcarbamate 2a can be isolated due to its stability and possibly converted subsequently into MDI44,45 offering new perspectives to regenerate diisocyanates. In doing so the ordinary artisan would have arrived at the methods of claim 16.
Concerning claim 21, MPEP 2144.05 I.: “In the case where the claimed ranges
“overlap or lie inside ranges disclosed by the prior art” a prima facie case of
obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning claim 22 and at least two polyurethanes, Zhao et al. teach different
possible MDI isomers and/or polymeric forms. Thus it would have been obvious to try to perform the alcoholysis on polyurethanes having at least two polyurethanes.
Concerning claim 23, upon utilizing the distillation taught by Bock et al. to distill the current product alcohol from the current isocyanate arrived at by the ordinary artisan, it would have been obvious to find the working temperature ranges for the distillation via routine experimentation. Too low of a temperature, the alcohol will not distill. Too high diminishing returns.
MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Concerning claim 24, MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).” The boiling point of methanol is a property of methanol. Alcoholysis temperatures were taught to be 55 or 65C.
Concerning claim 31, the ordinary artisan would have utilized methanol as the first alcohol to prepare the methylcarbamate compound 2a taught by Zhao et al. Upon, performing the thermolysis, methanol would have been made as the product alcohol.
Claim(s) 16, 21-22, 25-26 and 31 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hinzmann et al. (USPGPub 2025/0034606, foreign priority to EP21179237.9, filed 06-2021. All references to Hinzmann et al. are made to an
English translation of the claims and pages 6, 11, 19 and 22 of EP21179237.9.
See attached).
Scope of the Prior Art
The prior art reference Hinzmann et al. teach the individual steps of the claimed process in various locations in the reference document.
Hinzmann et al. teach the following.
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Step D.II is detailed on page 19 of Hinzmann et al. See immediately below.
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The separation of the alcohol is the current step (d).
Concerning claim 21 and 26, Hinzmann et al. teach the carbamate cleavage reaction can be carried out at 150 to 280C (p. 22).
Concerning claim 22 and 26 and at least two polyurethanes, Hinzmann et al.
teach different isocyanates and/or mixtures of isocyanates may be used and explicitly
points to methylene diphenyl diisocyanate (MDI) (p. 6).
Concerning claim 25 and the alcoholysis reaction temp., Hinzmann et al. teach 130 to 195C (p. 11).
Obviousness
From the limited options available to process the carbamate in Hinzmann et al., it would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have tried the thermolytic cleavage of the carbamate to prepare the isocyanate in isolated form with a reasonable expectation of success. MPEP 2141 (E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with
a reasonable expectation of success.
In doing so the ordinary artisan would have arrived at the current invention of claim 16.
Concerning claim 21 and 26, MPEP 2144.05 I.: “In the case where the claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of
obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning claim 22 and at least two polyurethanes, Hinzmann et al. teach different isocyanates and/or mixtures of isocyanates may be used. Thus it would have been obvious to try to perform the alcoholysis on polyurethanes having at least two polyurethanes.
Concerning claim 25, MPEP 2144.05 I.: “In the case where the claimed ranges
“overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976).”
Concerning claim 31, the ordinary artisan would have utilized araliphatic monofunctional alcohol as the first alcohol to prepare the carbamate compound taught by Hinzmann et al. Upon, performing the thermolysis, the araliphatic monofunctional alcohol would have been made as the product alcohol.
Claim(s) 23 is/are rejected under 35 U.S.C. 103 as being unpatentable over Hinzmann et al. (USPGPub 2025/0034606, foreign priority to EP21179237.9, filed 06-2021. All references to Hinzmann et al. are made to an English translation of the claims and pages 6, 11, 19 and 22 of EP21179237.9. See attached) as applied to claims 16, 21-22, 25-26 and 31 and in further view of Bock et al. (US Patent 8,680,323, Patent date 03-2014).
Scope of the Prior Art
The teachings of Hinzmann et al. are in the above 103 rejection and are incorporated by reference. As a reminder, Hinzmann et al. teach page 19 the separation of the alcohol from the isocyanate as seen immediately below.
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Ascertain the Differences
Hinzmann et al. does not teach distilling away the product alcohol at a temperature from about 100 to 300C when separating the isocyanate from the alcohol.
Secondary References
Bock et al. teach “The object is achieved by a process for preparing isocyanates by thermal dissociation of carbamates and separation by distillation of the reaction mixture from the carbamate dissociation, comprising the corresponding isocyanate and the corresponding alcohol, by distillation in a column having an enrichment section and a stripping section, where the carbamate is introduced between the enrichment section and the stripping section and the isocyanate is taken off as a constituent of the bottom stream and the alcohol is taken off as a constituent of the overhead stream from the column, in the presence of an inert solvent…” (column 2, lines 1-25).
Obviousness
It would have been prima facie obvious for an ordinary artisan before the effective filing date of the claimed invention to have utilized the separation method distillation taught by Bock et al. to separate the isocyanate and alcohol taught by Hinzmann et al. and arrive at the current invention.
The ordinary artisan would have done so with a reasonable expectation of success to satisfy a separation method. The reasonable expectation of success
Being Bock et al. teach “The object is achieved by a process for preparing isocyanates by thermal dissociation of carbamates and separation by distillation of the reaction mixture from the carbamate dissociation, comprising the corresponding isocyanate and the corresponding alcohol”.
The ordinary artisan would have looked to Bock et al. because Bock et al. and Hinzmann et al. teach overlapping methods, the thermolysis of carbamates to isocyanates and the corresponding alcohol with subsequent separation.
Concerning claim 23, upon utilizing the distillation taught by Bock et al. to distill
the current product alcohol from the current isocyanate arrived at by the ordinary artisan, it would have been obvious to find the working temperature ranges for the distillation via routine experimentation. Too low of a temperature, the alcohol will not distill. Too high diminishing returns.
MPEP 2144.05 II. A. and B. “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Allowable Subject Matter
The prior art does not pertain to Claim 17 for the following reasons. The closest prior art to the invention is Zhao et al. The teachings of Zhao et al. are in the above 103 rejections and are incorporated by reference. Bock et al. was brought in the teach current step (c) and (d) as written in the above 103 rejections and incorporated by reference.
Neither Zhao et al. alone nor in combination with Bock et al. teach glycolysis of polyurethane with ethylene glycol. Moreover, Zhao et al. teach the benefits of the use of methanol in the alcoholysis of polyurethane. See Zhao et al. page 4176 “This O-dimethylcarbamate is stable to be reformulated or isolated and reactive enough to form a new urethane bond with the elimination of MeOH allowing the regeneration of PU and page 4179, “ One important advantage of methanolysis is the production of O-methylcarbamate, a useful reactive intermediate that can be used to regenerate PUs through transcarbamoylation associated to the release of MeOH which can be easily
eliminated by evaporation during the reaction”.
Thus, it would not have been obvious to have modified the prior art with any other alcohol or ethylene glycol to arrive at the current invention. There being no motivation to do so.
With respect to reference Hinzmann et al., Hinzmann et al. teach the use of an araliphatic alcohol. This is not the alkyl alcohol ethylene glycol being claimed.
The prior art does not pertain to Claim 18 for the following reasons. The closest prior art to the invention is Zhao et al. The teachings of Zhao et al. are in the above 103 rejections and are incorporated by reference. Bock et al. was brought in the teach current steps (c) and (d), as written in the above 103 rejections and incorporated by reference.
Neither Zhao et al. alone nor in combination with Bock et al. teach step (b1), the transcarbamation of a second alcohol with the first carbamate nor the separation step (b2). Zhao et al. teach a single alcohol methanol and not the second alcohol.
For example, Zhao et al. teach the benefits of the use of methanol in the alcoholysis of polyurethane. Thus, it would not have been obvious to have modified the prior art to arrive at the current invention. There being no motivation to do so.
With respect to reference Hinzmann et al., Hinzmann et al. teach the use of an araliphatic alcohol and does not teach the use of a second alcohol in a transcarbamation.
Claims 19-20, 27-29 and 32 depend on claim 18.
Conclusion
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/B.G.D/ Examiner, Art Unit 1692 /Andrew D Kosar/Supervisory Patent Examiner, Art Unit 1625
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