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 .
Election/Restrictions
Applicant’s election of Group I, claims 1-12, in the reply filed on 10/07/2025 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Claims 13-18 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected inventions, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 10/07/2025.
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.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Claim Objections
Claims 1-12 are objected to because of the following informalities: Claims 1, 3, and 7 contain capitalized words other than at the beginning of the claim in lines 3, 5, and 7 of claim 1, in lines 3-15 of claim 3, and in lines 4, 6, 8, and 11 of claim 7 (see MPEP 608.01(m)). The Office suggests that Applicant change the capitalized words to the corresponding lower case words. 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 2, 5, 6, 8, and 10-12 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.
Claim 2 recites the limitation “the dianhydrohexitol is an isohexitol, preferably selected from isosorbide, isomannide or isoidide, and is, more preferably, isosorbide” in lines 1-3, which is indefinite because the terms “preferably” and “more preferably” make it unclear if it is required that the “isohexitol” is “selected from isosorbide, isomannide or isoidide” or “isosorbide”. For further examination of the claims, this limitation is interpreted as “the dianhydrohexitol is an isohexitol, isosorbide, isomannide, or isoidide”.
Claim 5 recites the limitation “a polyepoxide obtained by a method for curing an epoxy prepolymer composition obtained by a method for the etherification of the other alcohol with an epihalohydrin, preferably has a water uptake lower than the water uptake, measured according to the same method, of a polyepoxide obtained by the same curing and etherification methods but by replacing the other alcohol with dianhydrohexitol” in lines 2-6, which is indefinite because the term “preferably” makes it unclear if it is required that “a polyepoxide obtained by a method for curing an epoxy prepolymer composition obtained by a method for the etherification of the other alcohol with an epihalohydrin” “has a water uptake lower than the water uptake, measured according to the same method, of a polyepoxide obtained by the same curing and etherification methods but by replacing the other alcohol with dianhydrohexitol”. For further examination of the claims, this limitation is interpreted as “a polyepoxide obtained by a method for curing an epoxy prepolymer composition obtained by a method for the etherification of the other alcohol with an epihalohydrin, has a water uptake lower than the water uptake, measured according to the same method, of a polyepoxide obtained by the same curing and etherification methods but by replacing the other alcohol with dianhydrohexitol”.
Claim 6 recites the limitation “the epihalohydrin is selected from epibromohydrin, epifluorohydrin, epiiodohydrin, epichlorhydrin, or mixtures thereof, preferably epihalohydrin is epichlorhydrin” in lines 1-2, which is indefinite because the term “preferably” makes it unclear if it is required that “epihalohydrin is epichlorhydrin”. For further examination of the claims, this limitation is interpreted as “the epihalohydrin is selected from epibromohydrin, epifluorohydrin, epiiodohydrin, epichlorhydrin, or mixtures thereof”.
Claim 8 recites the limitation “the basic reagent is selected from lithium, potassium, calcium or sodium hydroxides, preferably in the form of an aqueous solution, and is more preferably an aqueous sodium hydroxide solution” in lines 1-3, which is indefinite because the terms ”preferably” and “more preferably” make it unclear if it is required that “the basic reagent” “selected from lithium, potassium, calcium or sodium hydroxides” “is” “in the form of an aqueous solution” and “is” “an aqueous sodium hydroxide solution”. For further examination of the claims, this limitation is interpreted as “the basic reagent is selected from lithium, potassium, calcium or sodium hydroxides”.
Claim 10 recites the limitation “the phase-transfer catalyst is selected from halides, tetraalkyl ammonium sulfates or hydrogen sulfates, preferably from tetrabutylammonium bromide or tetrabutylammonium iodide” in lines 1-3, which is indefinite because the term “preferably” makes it unclear if it is required that “the phase-transfer catalyst is selected” “from tetrabutylammonium bromide or tetrabutylammonium iodide”. For further examination of the claims, this limitation is interpreted as “the phase-transfer catalyst is selected from halides, tetraalkyl ammonium sulfates or hydrogen sulfates”.
Claim 11 recites the limitation “the amount of phase-transfer catalyst is comprised between 0.01 and 5%, preferably between 0.1% and 2%, more preferably is 1% by weight relative to the total represented by the sum of the masses of the dianhydrohexitol and of the other alcohol” in lines 2-4, which is indefinite because the terms “preferably” and “more preferably” make it unclear if it is required that “the amount of phase-transfer catalyst is comprised” “between 0.1% and 2%” or “is 1% by weight relative to the total represented by the sum of the masses of the dianhydrohexitol and of the other alcohol”. For further examination of the claims, this limitation is interpreted as “the amount of phase-transfer catalyst is comprised between 0.01 and 5 % relative to the total represented by the sum of the masses of the dianhydrohexitol and of the other alcohol”.
Claim 12 recites the limitation “preferably said filtration step is followed by a step of concentrating the filtrate and/or a step of purifying the filtrate” in lines 3-4, which is indefinite because the term “preferably” makes it unclear if it is required that “said filtration step is followed by a step of concentrating the filtrate and/or a step of purifying the filtrate”. For further examination of the claims, this limitation is interpreted as “optionally said filtration step is followed by a step of concentrating the filtrate and/or a step of purifying the filtrate”.
Claim Rejections - 35 USC § 103
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 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.
Claims 1-6 and 12 are rejected under 35 U.S.C. 103 as being unpatentable over Kim (KR 101906768 B1, machine translation in English or untranslated patent used for citation as indicated).
Regarding claims 1, 2, 4, and 6, Kim teaches a method for producing an aqueous crosslinking agent for surface treatment of polyester fibers (translation [0006]) comprising a first step of mixing a polyhydric alcohol and a first organic solvent at 80 to 100°C, a second step of adding a Lewis acid catalyst and epichlorohydrin to the mixture of the first step and performing a reaction by dropping the mixture at 60 to 90°C, a third step of adjusting the pH of the reaction mixture obtained according to the second step to neutral and performing a reaction thereon at 70 to 80°C, a fourth step of adding a strong alkaline aqueous solution to the reaction product of the third step and performing a condensation reaction, a fifth step of adding a second organic solvent and washing water to the reaction product obtained according to the fourth step to separate a salt layer and a resin layer, and a sixth step of recovering and removing a second organic solvent from the result obtained according to the fifth step (translation [0007], [0012]), wherein the above polyhydric alcohol is at least one selected from compounds represented by the following chemical formulas 1a, 1b, and 1c (translation [0016]), wherein formula 1a is
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(untranslated [0017]), formula 1b is
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(untranslated [0020]), and formula 1c is
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(untranslated [0023]), wherein R5 is -H (translation [0019], untranslated [0019]), R3 is -H, R4 is -OH (translation [0022], untranslated [0022]), R5 is -H, and R6 is -OH (translation [0025], untranslated [0025]), wherein a condensation reaction that is a glycidylation reaction of halohydrin ether is a result obtained through the process (translation [0060], [0079]), wherein the reaction in the second step is an epoxidation reaction (translation [0037], [0069], [0070], [0077], [0086], [0087]), which reads on a method for preparing an epoxy prepolymer composition comprising glycidyl ethers, said method comprising the following steps: a) placing a dianhydrohexitol and/or another alcohol into contacted with a dianhydrohexitol and/or another alcohol so as to obtain a composition of alcohols, b) reacting the composition of alcohols obtained in step a) with an epihalohydrin so as to obtain a reaction mixture comprising glycidyl ethers, c) recovering the epoxy prepolymer composition comprising glycidyl ethers from the reaction mixture obtained at the end of step b), wherein the dianhydrohexitol is an isohexitol, preferably selected from isosorbide, and is more preferably, isosorbide, wherein the other alcohol comprises three or four alcohol functions, wherein the epihalohydrin is selected from epichlorohydrin, preferably epihalohydrin is epichlorohydrin.
Kim does not teach a specific embodiment wherein the step a) is placing a dianhydrohexitol into contact with another alcohol so as to obtain a composition of alcohols, wherein the other alcohol comprises at least two alcohol functions. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Kim’s compound represented by formula 1c
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wherein R5 is -H and R6 is -OH and Kim’s compound represented by formula 1a
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wherein R5 is -H or formula 1b
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wherein R3 is -H and R4 is -OH as Kim’s polyhydric alcohol in Kim’s method. The proposed modification would read on the step a) is placing a dianhydrohexitol into contact with another alcohol so as to obtain a composition of alcohols as claimed, wherein the other alcohol comprises three or four alcohol functions as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of polyhydric alcohol that is suitable of Kim’s method or because it would have been obvious to try with a reasonable expectation of success because Kim teaches that the above polyhydric alcohol is at least one selected from compounds represented by the following chemical formulas 1a, 1b, and 1c (translation [0016]), wherein formula 1a is
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(untranslated [0017]), formula 1b is
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(untranslated [0020]), and formula 1c is
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(untranslated [0023]), wherein R5 is -H (translation [0019], untranslated [0019]), R3 is -H, R4 is -OH (translation [0022], untranslated [0022]), R5 is -H, and R6 is -OH (translation [0025], untranslated [0025]). Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 3, Kim teaches that the above polyhydric alcohol is at least one selected from compounds represented by the following chemical formulas 1a and 1c (translation [0016]), wherein formula 1a is
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(untranslated [0017]), and formula 1c is
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(untranslated [0023]), wherein R5 is -H (translation [0019], untranslated [0019]), R5 is -H, and R6 is -OH (translation [0025], untranslated [0025]), which optionally reads on wherein the other alcohol is selected from the following alcohol: - Trimethylol propane as claimed.
Kim does not teach a specific embodiment wherein the other alcohol is selected from the claimed alcohols. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select Kim’s compound represented by formula 1c
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wherein R5 is -H and R6 is -OH and Kim’s compound represented by formula 1a
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wherein R5 is -H as Kim’s polyhydric alcohol in Kim’s method. The proposed modification would read on wherein the other alcohol is selected from the following alcohol: - Trimethylol propane as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for providing a species of polyhydric alcohol that is suitable of Kim’s method or because it would have been obvious to try with a reasonable expectation of success because Kim teaches that the above polyhydric alcohol is at least one selected from compounds represented by the following chemical formulas 1a and 1c (translation [0016]), wherein formula 1a is
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(untranslated [0017]), and formula 1c is
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(untranslated [0023]), wherein R5 is -H (translation [0019], untranslated [0019]), R5 is -H, and R6 is -OH (translation [0025], untranslated [0025]). Examples of rationales that may support a conclusion of obviousness include "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success (MPEP 2143(I)(E)).
Regarding claim 5, the Office recognizes that all of the claimed physical properties are not positively taught by Kim, namely that a polyepoxide obtained by a method for curing an epoxy prepolymer composition obtained by a method for the etherification of the other alcohol with an epihalohydrin, preferably has a water uptake lower than the water uptake, measured according to the same method, of a polyepoxide obtained by the same curing and etherification methods but by replacing the other alcohol with dianhydrohexitol. However, Kim renders obvious all of the claimed ingredients, amounts, process steps, and process conditions of the metho according to claims 1-4, as explained above. Furthermore, the specification of the instant application recites that if the dianhydrohexitol and the other alcohol are mixed before the step of synthesizing the epoxy prepolymer, better properties are obtained, especially lower water uptake properties for the resulting polyepoxide, than for the polyepoxide obtained from the mixture of the epoxy prepolymers synthesized separately from the dianhydrohexitol and from the other alcohol [0038], that the present disclosure relates to the preparation of epoxy prepolymers comprising dianhydrohexitol glycidyl ethers allowing polyepoxides to be obtained with improved water uptake [0039], that the polyepoxides obtained by curing curable compositions comprising epoxy prepolymer compositions obtained by the method according to the invention exhibit properties, for example, water uptake properties, that are improved relative to the properties of polyepoxides obtained by curing comparable curable compositions resulting from mixing a dianhydrohexitol-based epoxy prepolymer and an epoxy prepolymer based on the other alcohol [0055], that the other alcohol brought into contact with a dianhydrohexitol in step a. of the method according to the invention is selected such that a polyepoxide based on said other alcohol has a lower water uptake than that of a polyepoxide based on said dianhydrohexitol [0061], that the other alcohol brought into contact with a dianhydrohexitol in step a. of the method according to the invention is selected such that a polyepoxide based on said other alcohol has a lower water uptake than that of a polyepoxide based on said dianhydrohexitol [0061], that a polyepoxide obtained by a method for curing an epoxy prepolymer composition obtained by means of a method for the etherification of the other alcohol with an epihalohydrin, preferably has a water uptake that is lower than the water uptake, measured according to the same method, of a polyepoxide obtained by the same curing and etherification methods but by replacing the other alcohol with dianhydrohexitol [0062], and that the polyepoxide according to the invention has a water uptake that is less than or equal to 15%, in particular comprised between 0.1% and 11%, more particularly between 0.5% and 9.5%, preferably between 1% and 9%, more particularly between 1.5% and 8.5%, even more particularly between 2% and 8% [0114]. Therefore, the claimed physical properties would naturally arise from the method that is rendered obvious by Kim. When the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent (MPEP 2112.01(I)). If the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present (MPEP 2112.01(II)). If it is the applicant’s position that this would not be the case: (1) evidence would need to be presented to support the applicant’s position; and (2) it would be the Office’s position that the application contains inadequate disclosure that there is no teaching as to how to obtain the claimed properties with only the claimed ingredients, amounts, process steps, and process conditions.
Regarding claim 12, Kim teaches that the method comprises a second step of adding a Lewis acid catalyst and epichlorohydrin to the mixture of the first step and performing a reaction by dropping the mixture at 60 to 90°C, a third step of adjusting the pH of the reaction mixture obtained according to the second step to neutral and performing a reaction thereon at 70 to 80°C, a fourth step of adding a strong alkaline aqueous solution to the reaction product of the third step and performing a condensation reaction, a fifth step of adding a second organic solvent and washing water to the reaction product obtained according to the fourth step to separate a salt layer and a resin layer, and a sixth step of recovering and removing a second organic solvent from the result obtained according to the fifth step (translation [0007], [0012]), that a seventh step of adding a phosphoric acid substance to the result obtained according to the sixth step may be further performed (translation [0042], [0043], [0062, [0071], [0080], [0088]), and that a filter is used to filter the mixture, thereby obtaining an aqueous crosslinking agent (translation [0043], [0062], [0071], [0080], [0088]), which reads on the method according to claim 1, wherein step c) comprises a step c) comprises a step of filtering the reaction medium obtained at the end of step b) so as to obtain a filtrate comprising the epoxy prepolymer composition as claimed. Kim satisfies the limitation “preferably said filtration step is followed by a step of concentrating the filtrate and/or a step of purifying the filtrate” as claimed because it is interpreted as being an optional limitation.
Claims 1-12 are rejected under 35 U.S.C. 103 as being unpatentable over Buffe et al. (US 2017/0002132 A1) in view of Kim (KR 101906768 B1, machine translation in English or untranslated patent used for citation as indicated).
Regarding claims 1, 4, and 12, Buffe teaches a process for producing a bis-anhydrohexitol ether composition comprising the following steps: [0022] a) bringing a dianhydrohexitol into contact with an organic halide [0023], b) placing the resulting mixture of dianhydrohexitol and organic halide under vacuum so as to obtain a negative pressure of between 100 mbar and 1000 mbar [0024], c) heating the mixture under vacuum at a temperature of between 50° C and 120° C and thus carrying out an azeotropic distillation [0025], d) then adding to said mixture a basic reagent for a period of between 1 hour and 10 hours and then continuing the azeotropic distillation [0026], e) recovering the bis-anhydrohexitol ether composition after a filtration step, concentration of the filtering and optionally a purification step [0027], wherein this process results in compositions with a very high richness in diepoxy derivatives of isosorbide [0021], wherein the organic halide is chosen from epibromohydrin, epifluorohydrin, epiiodohydrin and epichlorohydrin [0032], wherein the bis-anhydrohexitol ether is a dianhydrohexitol diglycidyl ether [0048, 0064, 0076, 0082, 0090, 0091, 0092, 0097], which reads on a method for preparing an epoxy prepolymer composition comprising glycidyl ethers, said method comprising the following steps: a) Placing a dianhydrohexitol into contact with dianhydrohexitol so as to obtain a composition of an alcohol, b) Reacting the composition of alcohol obtained in step a) with an epihalohydrin so as to obtain a reaction mixture comprising glycidyl ethers, c) Recovering the epoxy prepolymer composition comprising glycidyl ethers from the reaction mixture obtained at the end of step b), wherein step c) comprises a step of filtering the reaction medium obtained at the end of step b) so as to obtain a filtrate comprising the epoxy prepolymer composition, preferably said filtration step is followed by a step of concentrating the filtrate and/or a step of purifying the filtrate.
Buffe does not teach that said method comprises the following step: a) Placing a dianhydrohexitol into contact with another alcohol so as to obtain composition of alcohols, that the composition of alcohol in step b) is the composition of alcohols, and that the other alcohol comprises at least two alcohol functions. However, Kim teaches a polyhydric alcohol that is at least one selected from compounds represented by the following chemical formulas 1a, 1b, and 1c (translation [0016]), wherein formula 1a is
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(untranslated [0017]), formula 1b is
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(untranslated [0020]), and formula 1c is
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(untranslated [0023]), wherein R5 is -H (translation [0019], untranslated [0019]), R3 is -H, R4 is -OH (translation [0022], untranslated [0022]), R5 is -H, and R6 is -OH (translation [0025], untranslated [0025]), wherein the polyhydric alcohol is used (translation [0007], [0012]) in a method for producing an aqueous crosslinking agent for surface treatment of polyester fibers (translation [0006]) comprising a first step of mixing a polyhydric alcohol and a first organic solvent at 80 to 100°C, a second step of adding a Lewis acid catalyst and epichlorohydrin to the mixture of the first step and performing a reaction by dropping the mixture at 60 to 90°C, a third step of adjusting the pH of the reaction mixture obtained according to the second step to neutral and performing a reaction thereon at 70 to 80°C, a fourth step of adding a strong alkaline aqueous solution to the reaction product of the third step and performing a condensation reaction, a fifth step of adding a second organic solvent and washing water to the reaction product obtained according to the fourth step to separate a salt layer and a resin layer, and a sixth step of recovering and removing a second organic solvent from the result obtained according to the fifth step (translation [0007], [0012]), wherein a condensation reaction that is a glycidylation reaction of halohydrin ether is a result obtained through the process (translation [0060], [0079]), wherein the reaction in the second step is an epoxidation reaction (translation [0037], [0069], [0070], [0077], [0086], [0087]). Buffe and Kim are analogous art because both references are in the same field of endeavor of a method for preparing an epoxy prepolymer composition comprising glycidyl ethers comprising reacting a composition of an alcohol comprising a dianhydrohexitol with an epihalohydrin so as to obtain a reaction mixture comprising glycidyl ethers, and recovering the epoxy prepolymer composition comprising glycidyl ethers from the reaction mixture. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kim’s compound represented by formula 1a
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wherein R5 is -H or formula 1b
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wherein R3 is -H and R4 is -OH to substitute for a fraction of Buffe’s dianhydrohexitol in Buffe’s process. The proposed modification would read on said method comprising the following step: a) Placing a dianhydrohexitol into contact with another alcohol so as to obtain composition of alcohols, and the composition of alcohol in step b) is the composition of alcohols as claimed, wherein the other alcohol comprises two or four alcohol functions as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying reaction properties with Buffe’s organic halide in Buffe’s process because Kim teaches that a polyhydric alcohol that is at least one selected from compounds represented by the following chemical formulas 1a, 1b, and 1c (translation [0016]), wherein formula 1a is
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(untranslated [0017]), formula 1b is
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(untranslated [0020]), and formula 1c is
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(untranslated [0023]), wherein R5 is -H (translation [0019], untranslated [0019]), R3 is -H, R4 is -OH (translation [0022], untranslated [0022]), R5 is -H, and R6 is -OH (translation [0025], untranslated [0025]), is beneficial for being useful (translation [0007], [0012]) in a method (translation [0006]) comprising a first step of mixing a polyhydric alcohol and a first organic solvent at 80 to 100°C, a second step of adding a Lewis acid catalyst and epichlorohydrin to the mixture of the first step and performing a reaction by dropping the mixture at 60 to 90°C, a third step of adjusting the pH of the reaction mixture obtained according to the second step to neutral and performing a reaction thereon at 70 to 80°C, a fourth step of adding a strong alkaline aqueous solution to the reaction product of the third step and performing a condensation reaction, a fifth step of adding a second organic solvent and washing water to the reaction product obtained according to the fourth step to separate a salt layer and a resin layer, and a sixth step of recovering and removing a second organic solvent from the result obtained according to the fifth step (translation [0007], [0012]), wherein a condensation reaction that is a glycidylation reaction of halohydrin ether is a result obtained through the process (translation [0060], [0079]), wherein the reaction in the second step is an epoxidation reaction (translation [0037], [0069], [0070], [0077], [0086], [0087]), and because Buffe teaches that the dianhydrohexitol is preferentially an isohexitol, more preferentially chosen from isosorbide, isomannide and isoidide [0031], and that the dianhydrohexitol is used [0023] in a process for producing a bis-anhydrohexitol ether composition comprising the following steps: [0022] a) bringing a dianhydrohexitol into contact with an organic halide [0023], b) placing the resulting mixture of dianhydrohexitol and organic halide under vacuum so as to obtain a negative pressure of between 100 mbar and 1000 mbar [0024], c) heating the mixture under vacuum at a temperature of between 50° C and 120° C and thus carrying out an azeotropic distillation [0025], d) then adding to said mixture a basic reagent for a period of between 1 hour and 10 hours and then continuing the azeotropic distillation [0026], e) recovering the bis-anhydrohexitol ether composition after a filtration step, concentration of the filtering and optionally a purification step [0027], wherein this process results in compositions with a very high richness in diepoxy derivatives of isosorbide [0021], wherein the organic halide is chosen from epibromohydrin, epifluorohydrin, epiiodohydrin and epichlorohydrin [0032], wherein the bis-anhydrohexitol ether is a dianhydrohexitol diglycidyl ether [0048, 0064, 0076, 0082, 0090, 0091, 0092, 0097], which means that Kim’s compound and Buffe’s dianhydrohexitol are both present with a dianhydrohexitol and are reacted with epichlorohydrin in a method that prepares a glycidyl ether.
Regarding claim 2, Buffe teaches that the dianhydrohexitol is an isohexitol, preferentially chosen from isosorbide, isomannide and isoidide, and is, more preferentially, isosorbide [0031], which reads on wherein the dianhydrohexitol is an isohexitol, preferably selected from isosorbide, isomannide or isoidide, and is, more preferably. Isosorbide as claimed.
Regarding claim 3, Buffe does not teach that the other alcohol is selected from the claimed alcohols. However, Kim teaches a polyhydric alcohol that is at least one selected from compounds represented by the following chemical formulas 1a and 1c (translation [0016]), wherein formula 1a is
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(untranslated [0017]), and formula 1c is
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(untranslated [0023]), wherein R5 is -H (translation [0019], untranslated [0019]), R5 is -H, and R6 is -OH (translation [0025], untranslated [0025]), wherein the polyhydric alcohol is used (translation [0007], [0012]) in a method for producing an aqueous crosslinking agent for surface treatment of polyester fibers (translation [0006]) comprising a first step of mixing a polyhydric alcohol and a first organic solvent at 80 to 100°C, a second step of adding a Lewis acid catalyst and epichlorohydrin to the mixture of the first step and performing a reaction by dropping the mixture at 60 to 90°C, a third step of adjusting the pH of the reaction mixture obtained according to the second step to neutral and performing a reaction thereon at 70 to 80°C, a fourth step of adding a strong alkaline aqueous solution to the reaction product of the third step and performing a condensation reaction, a fifth step of adding a second organic solvent and washing water to the reaction product obtained according to the fourth step to separate a salt layer and a resin layer, and a sixth step of recovering and removing a second organic solvent from the result obtained according to the fifth step (translation [0007], [0012]), wherein a condensation reaction that is a glycidylation reaction of halohydrin ether is a result obtained through the process (translation [0060], [0079]), wherein the reaction in the second step is an epoxidation reaction (translation [0037], [0069], [0070], [0077], [0086], [0087]). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Kim’s compound represented by formula 1a
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wherein R5 is -H to substitute for a fraction of Buffe’s dianhydrohexitol in Buffe’s process. The proposed modification would read on wherein the other alcohol is selected from the following alcohol: - Trimethylol propane as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for modifying reaction properties with Buffe’s organic halide in Buffe’s process because Kim teaches that a polyhydric alcohol that is at least one selected from compounds represented by the following chemical formulas 1a and 1c (translation [0016]), wherein formula 1a is
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(untranslated [0017]), and formula 1c is
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(untranslated [0023]), wherein R5 is -H (translation [0019], untranslated [0019]), R5 is -H, and R6 is -OH (translation [0025], untranslated [0025]), is beneficial for being useful (translation [0007], [0012]) in a method (translation [0006]) comprising a first step of mixing a polyhydric alcohol and a first organic solvent at 80 to 100°C, a second step of adding a Lewis acid catalyst and epichlorohydrin to the mixture of the first step and performing a reaction by dropping the mixture at 60 to 90°C, a third step of adjusting the pH of the reaction mixture obtained according to the second step to neutral and performing a reaction thereon at 70 to 80°C, a fourth step of adding a strong alkaline aqueous solution to the reaction product of the third step and performing a condensation reaction, a fifth step of adding a second organic solvent and washing water to the reaction product obtained according to the fourth step to separate a salt layer and a resin layer, and a sixth step of recovering and removing a second organic solvent from the result obtained according to the fifth step (translation [0007], [0012]), wherein a condensation reaction that is a glycidylation reaction of halohydrin ether is a result obtained through the process (translation [0060], [0079]), wherein the reaction in the second step is an epoxidation reaction (translation [0037], [0069], [0070], [0077], [0086], [0087]), and because Buffe teaches that the dianhydrohexitol is preferentially an isohexitol, more preferentially chosen from isosorbide, isomannide and isoidide [0031], and that the dianhydrohexitol is used [0023] in a process for producing a bis-anhydrohexitol ether composition comprising the following steps: [0022] a) bringing a dianhydrohexitol into contact with an organic halide [0023], b) placing the resulting mixture of dianhydrohexitol and organic halide under vacuum so as to obtain a negative pressure of between 100 mbar and 1000 mbar [0024], c) heating the mixture under vacuum at a temperature of between 50° C and 120° C and thus carrying out an azeotropic distillation [0025], d) then adding to said mixture a basic reagent for a period of between 1 hour and 10 hours and then continuing the azeotropic distillation [0026], e) recovering the bis-anhydrohexitol ether composition after a filtration step, concentration of the filtering and optionally a purification step [0027], wherein this process results in compositions with a very high richness in diepoxy derivatives of isosorbide [0021], wherein the organic halide is chosen from epibromohydrin, epifluorohydrin, epiiodohydrin and epichlorohydrin [0032], wherein the bis-anhydrohexitol ether is a dianhydrohexitol diglycidyl ether [0048, 0064, 0076, 0082, 0090, 0091, 0092, 0097], which means that Kim’s compound and Buffe’s dianhydrohexitol are both present with a dianhydrohexitol and are reacted with epichlorohydrin in a method that prepares a glycidyl ether.
Regarding claim 5, the Office recognizes that all of the claimed physical properties are not positively taught by Buffe, namely that a polyepoxide obtained by a method for curing an epoxy prepolymer composition obtained by a method for the etherification of the other alcohol with an epihalohydrin, preferably has a water uptake lower than the water uptake, measured according to the same method, of a polyepoxide obtained by the same curing and etherification methods but by replacing the other alcohol with dianhydrohexitol. However, Buffe in view of Kim renders obvious all of the claimed ingredients, amounts, process steps, and process conditions of the metho according to claims 1-4, as explained above. Furthermore, the specification of the instant application recites that if the dianhydrohexitol and the other alcohol are mixed before the step of synthesizing the epoxy prepolymer, better properties are obtained, especially lower water uptake properties for the resulting polyepoxide, than for the polyepoxide obtained from the mixture of the epoxy prepolymers synthesized separately from the dianhydrohexitol and from the other alcohol [0038], that the present disclosure relates to the preparation of epoxy prepolymers comprising dianhydrohexitol glycidyl ethers allowing polyepoxides to be obtained with improved water uptake [0039], that the polyepoxides obtained by curing curable compositions comprising epoxy prepolymer compositions obtained by the method according to the invention exhibit properties, for example, water uptake properties, that are improved relative to the properties of polyepoxides obtained by curing comparable curable compositions resulting from mixing a dianhydrohexitol-based epoxy prepolymer and an epoxy prepolymer based on the other alcohol [0055], that the other alcohol brought into contact with a dianhydrohexitol in step a. of the method according to the invention is selected such that a polyepoxide based on said other alcohol has a lower water uptake than that of a polyepoxide based on said dianhydrohexitol [0061], that the other alcohol brought into contact with a dianhydrohexitol in step a. of the method according to the invention is selected such that a polyepoxide based on said other alcohol has a lower water uptake than that of a polyepoxide based on said dianhydrohexitol [0061], that a polyepoxide obtained by a method for curing an epoxy prepolymer composition obtained by means of a method for the etherification of the other alcohol with an epihalohydrin, preferably has a water uptake that is lower than the water uptake, measured according to the same method, of a polyepoxide obtained by the same curing and etherification methods but by replacing the other alcohol with dianhydrohexitol [0062], and that the polyepoxide according to the invention has a water uptake that is less than or equal to 15%, in particular comprised between 0.1% and 11%, more particularly between 0.5% and 9.5%, preferably between 1% and 9%, more particularly between 1.5% and 8.5%, even more particularly between 2% and 8% [0114]. Therefore, the claimed physical properties would naturally arise from the method that is rendered obvious by Buffe in view of Kim. When the structure recited in the reference is substantially identical to that of the claims, claimed properties or functions are presumed to be inherent (MPEP 2112.01(I)). If the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present (MPEP 2112.01(II)). If it is the applicant’s position that this would not be the case: (1) evidence would need to be presented to support the applicant’s position; and (2) it would be the Office’s position that the application contains inadequate disclosure that there is no teaching as to how to obtain the claimed properties with only the claimed ingredients, amounts, process steps, and process conditions.
Regarding claim 6, Buffe teaches that the organic halide is chosen from epibromohydrin, epifluorohydrin, epiiodohydrin and epichlorohydrin, and is, more preferentially, isosorbide [0031], which reads on wherein the epihalohydrin is selected from epibromohydrin, epifluorohydrin, epiiodohydrin, epichlorhydrin, or mixtures thereof, preferably epihalohydrin is epichlorhydrin as claimed.
Regarding claim 7, Buffe teaches that the process for producing a bis-anhydrohexitol ether composition comprises the following steps: [0022] a) bringing a dianhydrohexitol into contact with an organic halide [0023], b) placing the resulting mixture of dianhydrohexitol and organic halide under vacuum so as to obtain a negative pressure of between 100 mbar and 1000 mbar [0024], c) heating the mixture under vacuum at a temperature of between 50° C and 120° C and thus carrying out an azeotropic distillation [0025], d) then adding to said mixture a basic reagent for a period of between 1 hour and 10 hours and then continuing the azeotropic distillation [0026], e) recovering the bis-anhydrohexitol ether composition after a filtration step, concentration of the filtering and optionally a purification step [0027], wherein this process results in compositions with a very high richness in diepoxy derivatives of isosorbide [0021], wherein the organic halide is preferentially chosen from epibromohydrin, epifluorohydrin, epiiodohydrin and epichlorohydrin [0032], wherein the bis-anhydrohexitol ether is a dianhydrohexitol diglycidyl ether [0048, 0064, 0076, 0082, 0090, 0091, 0092, 0097], wherein the distillation involves the mixture of water and organic halide [0043], wherein the azeotropic distillation is continued until complete elimination of the water [0044], which reads on wherein step b) of reacting the composition of alcohols with epihalohydrin comprises the following step: b1) Placing the composition of alcohols into contact with epihalohydrin so as to obtain a reaction mixture, b2) Placing the reaction mixture obtained in step b1) under vacuum so as to obtain a negative pressure comprised between 100 mbar and 1,000 mbar, b3) Heating the reaction mixture obtained in step b2), while maintaining said negative pressure, at a temperature comprised between 50°C and 120°C, so as to achieve distillation of the epihalohydrate, b4) Adding a basic reagent to the reaction mixture obtained in step b3) for a period comprised between 1 hour and 10 hours while maintaining the reaction mixture at said negative pressure and at said temperature so as to achieve azeotropic distillation of the water-epihalohydrin azeotrope as claimed.
Regarding claim 8, Buffe teaches that the basic reagent is chosen from lithium hydroxide, potassium hydroxide, calcium hydroxide and sodium hydroxide optionally in the form of an aqueous solution, and is, very preferentially, an aqueous solution of sodium hydroxide [0042], which reads on wherein the basic reagent is selected from lithium, potassium, calcium or sodium hydroxides, preferably in the form of an aqueous solution, and is more preferably an aqueous sodium hydroxide solution as claimed.
Regarding claim 9, Buffe teaches that a phase-transfer catalyst is added during the first step (step a) [0045], which reads on wherein a phase-transfer catalyst is added during step b1) as claimed.
Regarding claim 10, Buffe teaches that the phase-transfer catalyst is chosen from tetraalkylammonium halides, sulfates or hydrogen sulfates, and more preferentially from tetrabutylammonium bromide and tetrabutylammonium iodide [0046], which reads on wherein the phase-transfer catalyst is selected from halides, tetraalkyl ammonium sulfates or hydrogen sulfates, preferably from tetrabutylammonium bromide or tetrabutylammonium iodide as claimed.
Regarding claim 11, Buffe teaches that the amount of phase-transfer catalyst is between 0.01% and 5%, preferentially between 0.1% and 2%, more preferentially 1% by weight relative to the dianhydrohexitol [0046]. As explained above for claim 1, Buffe in view of Kim renders it obvious to use Kim’s compound represented by formula 1a
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wherein R5 is -H or formula 1b
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wherein R3 is -H and R4 is -OH to substitute for a fraction of Buffe’s dianhydrohexitol in Buffe’s process. Therefore, Buffe in view of Kim renders it obvious wherein the amount of phase-transfer catalyst is comprised between 0.01 and 5%, preferably between 0.1% and 2%, more preferably is 1% by weight relative to the total represented by the sum of the masses of the dianhydrohexitol and of the other alcohol as claimed.
Double Patenting
The nonstatutory double patenting rejection is based on a judicially created doctrine grounded in public policy (a policy reflected in the statute) so as to prevent the unjustified or improper timewise extension of the “right to exclude” granted by a patent and to prevent possible harassment by multiple assignees. A nonstatutory double patenting rejection is appropriate where the conflicting claims are not identical, but at least one examined application claim is not patentably distinct from the reference claim(s) because the examined application claim is either anticipated by, or would have been obvious over, the reference claim(s). See, e.g., In re Berg, 140 F.3d 1428, 46 USPQ2d 1226 (Fed. Cir. 1998); In re Goodman, 11 F.3d 1046, 29 USPQ2d 2010 (Fed. Cir. 1993); In re Longi, 759 F.2d 887, 225 USPQ 645 (Fed. Cir. 1985); In re Van Ornum, 686 F.2d 937, 214 USPQ 761 (CCPA 1982); In re Vogel, 422 F.2d 438, 164 USPQ 619 (CCPA 1970); In re Thorington, 418 F.2d 528, 163 USPQ 644 (CCPA 1969).
A timely filed terminal disclaimer in compliance with 37 CFR 1.321(c) or 1.321(d) may be used to overcome an actual or provisional rejection based on nonstatutory double patenting provided the reference application or patent either is shown to be commonly owned with the examined application, or claims an invention made as a result of activities undertaken within the scope of a joint research agreement. See MPEP § 717.02 for applications subject to examination under the first inventor to file provisions of the AIA as explained in MPEP § 2159. See MPEP § 2146 et seq. for applications not subject to examination under the first inventor to file provisions of the AIA . A terminal disclaimer must be signed in compliance with 37 CFR 1.321(b).
The filing of a terminal disclaimer by itself is not a complete reply to a nonstatutory double patenting (NSDP) rejection. A complete reply requires that the terminal disclaimer be accompanied by a reply requesting reconsideration of the prior Office action. Even where the NSDP rejection is provisional the reply must be complete. See MPEP § 804, subsection I.B.1. For a reply to a non-final Office action, see 37 CFR 1.111(a). For a reply to final Office action, see 37 CFR 1.113(c). A request for reconsideration while not provided for in 37 CFR 1.113(c) may be filed after final for consideration. See MPEP §§ 706.07(e) and 714.13.
The USPTO Internet website contains terminal disclaimer forms which may be used. Please visit www.uspto.gov/patent/patents-forms. The actual filing date of the application in which the form is filed determines what form (e.g., PTO/SB/25, PTO/SB/26, PTO/AIA /25, or PTO/AIA /26) should be used. A web-based eTerminal Disclaimer may be filled out completely online using web-screens. An eTerminal Disclaimer that meets all requirements is auto-processed and approved immediately upon submission. For more information about eTerminal Disclaimers, refer to www.uspto.gov/patents/apply/applying-online/eterminal-disclaimer.
Claims 1-12 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 2-7 and 9 of U.S. Patent No. 10,174,152 B2 in view of Kim (KR 101906768 B1, machine translation in English or untranslated patent used for citation as indicated).
The patent claims a process for producing bis-anhydrohexitol e