DETAILED ACTION
Applicant’s response filed on 06/01/2026 has been fully considered. Claims 1-15 are pending. Claim 12 is amended.
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 .
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 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 1-5, 7, 9, 11-13, and 15 are rejected under 35 U.S.C. 103 as being unpatentable over De Brouwer et al. (WO 2012/150560 A1, cited in IDS, made of record on 06/29/2023).
Regarding claims 1 and 9, De Brouwer teaches a method for the production of bisphenol A comprising contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter, wherein the method does not comprises a pretreatment and/purification step for the phenol and ketone [0017], wherein the ketone is acetone [0109, 0110, 0112], wherein the phenol starting materials can be commercial grade or better [0107], wherein as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], where in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], wherein these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], wherein the promoter catalyst system can tolerate impurities in reactant and/or recycle streams [0101], where in one aspect, at least a portion of the promoter is ionically bound to the available acid sites of the ion exchange resin [0125], where in another aspect, at least a portion of the promoter is covalently bound to at least a portion of the ion exchange resin [0125], where in yet another aspect, the degree of attachment or binding between a promoter and an ion exchange resin can vary, such as, for example, covalent binding, ionic binding, and/or other interactions or attraction forces [0125], wherein the promoter is not intended to be limited to any particular degree of attachment [0125], wherein the dimethyl thiazolidine attached promoter catalyst system can tolerate phenol and alcohol impurities without reducing the lifetime of the catalyst system [0127], wherein the dimethyl thiazolidine attached promoter catalyst system can tolerate other impurities detrimental to conventional catalyst systems [0127], wherein the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], wherein the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138], which reads on a process for preparing ortho,para- and/or para,para-bisphenol A, comprising the step of (a) condensing raw phenol and raw acetone in the presence of a catalyst system, wherein the catalyst system comprises an ion exchange resin catalyst and a sulfur containing cocatalyst, wherein the amount of 2-methyl benzofuran present in step (a) is higher than 0 ppm with respect to the total weight of the raw phenol, wherein the 2-methyl benzofuran present in step (a) is introduced into the process step (a) as impurity in the raw phenol, and which means that optionally, at least a portion of De Brouwer’s dimethyl thiazolidine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin, which optionally reads on wherein at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a).
De Brouwer does not teach that the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol, and does not teach a specific embodiment wherein the 2-methyl benzofuran present in step (a) is introduced into the process step (a) as impurity in the raw phenol. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the amount of methyl benzofuran in De Brouwer’s phenol in De Brouwer’s method to be greater than 1 ppm with respect to the weight of De Brouwer’s phenol. The proposed modification would read on wherein the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol as claimed, wherein step (a) is conducted in the additional presence of at least one impurity formed due to the presence of 2-methyl benzofuran in step (a) as claimed, wherein the 2-methyl benzofuran present in step (a) is introduced into the process step (a) as impurity in the raw phenol as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing the lifetime of De Bouwer’s catalyst system in De Bouwer’s method, and for optimizing the reaction rates in De Bouwer’s method because De Bouwer teaches that the method does not comprises a pretreatment and/purification step for the phenol and ketone [0017], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], that these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], that the promoter catalyst system can tolerate impurities in reactant and/or recycle streams [0101], that the dimethyl thiazolidine attached promoter catalyst system can tolerate phenol and alcohol impurities without reducing the lifetime of the catalyst system [0127], and that the dimethyl thiazolidine attached promoter catalyst system can tolerate other impurities detrimental to conventional catalyst systems [0127], which means that the amount of methyl benzofuran in De Brouwer’s phenol in De Brouwer’s method in ppm with respect to the weight of De Brouwer’s phenol would have affected the lifetime of De Bouwer’s catalyst system in De Bouwer’s method, and the reaction rates in De Bouwer’s method.
De Brouwer does not teach a specific embodiment wherein at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select De Brouwer’s dimethyl thiazolindine and De Brouwer’s ion exchange resin in De Brouwer’s method, such that at least a portion of De Brouwer’s dimethyl thiazolindine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin. The proposed modification would read on wherein at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been obvious to try with a reasonable expectation of success because De Brouwer teaches that the dimethyl thiazolidine is a promoter [0120], that in one aspect, at least a portion of the promoter is ionically bound to the available acid sites of the ion exchange resin [0125], that in another aspect, at least a portion of the promoter is covalently bound to at least a portion of the ion exchange resin [0125], that in still another aspect, all or substantially all of the promoter is at least covalently bound to the ion exchange resin [0125], that in yet another aspect, the degree of attachment or binding between a promoter and an ion exchange resin can vary, such as, for example, covalent binding, ionic binding, and/or other interactions or attraction forces [0125], and that the promoter is not intended to be limited to any particular degree of attachment [0125], which means that optionally, at least a portion of De Brouwer’s dimethyl thiazolidine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin. 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 2, De Brouwer teaches that the method does not comprise a pretreatment and/purification step for the phenol and ketone [0017], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], that these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], that the promoter catalyst system can tolerate impurities in reactant and/or recycle streams [0101], that the dimethyl thiazolidine attached promoter catalyst system can tolerate phenol and alcohol impurities without reducing the lifetime of the catalyst system [0127], and that the dimethyl thiazolidine attached promoter catalyst system can tolerate other impurities detrimental to conventional catalyst systems [0127], which reads on wherein the amount of 2-methyl benzofuran present in step (a) is higher than 0 ppm with respect to the total weight of the raw phenol.
De Brouwer does not teach that the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm and equal to or lower than 5000 ppm with respect to the total weight of the raw phenol. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the amount of methyl benzofuran in De Brouwer’s phenol in De Brouwer’s method to be greater than 1 ppm and less than 5000 ppm with respect to the weight of De Brouwer’s phenol. The proposed modification would read on wherein the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm and equal to or lower than 5000 ppm with respect to the total weight of the raw phenol as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing the lifetime of De Bouwer’s catalyst system in De Bouwer’s method, and for optimizing the reaction rates in De Bouwer’s method because De Bouwer teaches that the method does not comprises a pretreatment and/purification step for the phenol and ketone [0017], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], that these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], that the promoter catalyst system can tolerate impurities in reactant and/or recycle streams [0101], that the dimethyl thiazolidine attached promoter catalyst system can tolerate phenol and alcohol impurities without reducing the lifetime of the catalyst system [0127], and that the dimethyl thiazolidine attached promoter catalyst system can tolerate other impurities detrimental to conventional catalyst systems [0127], which means that the amount of methyl benzofuran in De Brouwer’s phenol in De Brouwer’s method in ppm with respect to the weight of De Brouwer’s phenol would have affected the lifetime of De Bouwer’s catalyst system in De Bouwer’s method, and the reaction rates in De Bouwer’s method.
Regarding claim 3, De Brouwer teaches that the method does not comprise a pretreatment and/purification step for the phenol and ketone [0017], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that the bisphenol A can comprise any combination of components, purities, and properties described therein, including various aspects wherein any individual component, purity, and/or property, such as, for example, organic purity can be either included or excluded from the composition [0152], and that thus, combinations wherein comprising any one or more components, purities, and/or properties, but excluding other components, purities, and/or properties recited therein are contemplated [0152]. As explained above for claim 1, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the amount of methyl benzofuran in De Brouwer’s phenol in De Brouwer’s method to be greater than 1 ppm with respect to the weight of De Brouwer’s phenol. Therefore, De Brouwer renders it obvious wherein step (a) is conducted in the additional presence of at least one impurity formed due to the presence of 2-methyl benzofuran in step (a) as claimed.
Regarding claim 4, De Brouwer teaches that the method does not comprise a pretreatment and/purification step for the phenol and ketone [0017], that the phenol starting materials can be commercial grade or better [0107], and that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107]. As explained above for claim 1, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the amount of methyl benzofuran in De Brouwer’s phenol in De Brouwer’s method to be greater than 1 ppm with respect to the weight of De Brouwer’s phenol. Therefore, De Brouwer renders it obvious wherein the 2-methyl benzofuran is present throughout the whole process step (a) as claimed.
Regarding claim 5, De Brouwer teaches that the method for the production of bisphenol A comprises contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter [0017], that the ketone is acetone [0109, 0110, 0112], that the bisphenol A can comprise any combination of components, purities, and properties described therein, including various aspects wherein any individual component, purity, and/or property, such as, for example, organic purity can be either included or excluded from the composition [0152], that thus, combinations wherein comprising any one or more components, purities, and/or properties, but excluding other components, purities, and/or properties recited therein are contemplated [0152], that the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], and that the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138], which suggests separating the product of De Brouwer’s step of contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter in De Brouwer’s method into a fraction comprising De Brouwer’s p,p-bisphenol A and o,p-bisphenol A and into a fraction comprising De Brouwer’s phenol that is unreacted, De Brouwer’s ketone that is acetone that is unreacted, and De Brouwer’s impurities that comprise methyl benzofuran, which suggests wherein the process further comprises the following step: (b) separating the mixture obtained after step (a) into a bisphenol A fraction comprising at least one of ortho,para- or para,para-bisphenol A and a phenol fraction, wherein the phenol fraction comprises unreacted phenol and at least one impurity formed due to the presence of 2-methyl benzofuran in step (a) as claimed.
De Brouwer does not teach a specific embodiment wherein the process further comprises the following step: (b) separating the mixture obtained after step (a) into a bisphenol A fraction comprising at least one of ortho,para-, ortho,ortho-, or para,para-bisphenol A and a phenol fraction, wherein the phenol fraction comprises unreacted phenol and at least one impurity formed due to the presence of 2-methyl benzofuran in step (a). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to separate the product of De Brouwer’s step of contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter in De Brouwer’s method into a fraction comprising De Brouwer’s p,p-bisphenol A and o,p-bisphenol A and into a fraction comprising De Brouwer’s phenol that is unreacted, De Brouwer’s ketone that is acetone that is unreacted, and De Brouwer’s impurities that comprise methyl benzofuran. The proposed modification would read on wherein the process further comprises the following step: (b) separating the mixture obtained after step (a) into a bisphenol A fraction comprising at least one of ortho,para- or para,para-bisphenol A and a phenol fraction, wherein the phenol fraction comprises unreacted phenol and at least one impurity formed due to the presence of 2-methyl benzofuran in step (a) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for purifying De Brouwer’s bisphenol A that is produced in De Brouwer’s method for the production of bisphenol A because De Brouwer teaches that the method for the production of bisphenol A comprises contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter [0017], that the ketone is acetone [0109, 0110, 0112], that the bisphenol A can comprise any combination of components, purities, and properties described therein, including various aspects wherein any individual component, purity, and/or property, such as, for example, organic purity can be either included or excluded from the composition [0152], that thus, combinations wherein comprising any one or more components, purities, and/or properties, but excluding other components, purities, and/or properties recited therein are contemplated [0152], that the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], and that the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138].
Regarding claim 7, De Brouwer teaches that when using a recycled phenol stream, the dimethyl thiazolidine catalyst system can provide levels of p,p-bisphenol A that are within about 10 %, within about 8 %, without about 6 %, within about 4 %, or within about 2 % of values obtained using a fresh phenol stream [0134], that when using a recycled phenol stream, the dimethyl thiazolidine catalyst system can provide levels of p,p-bisphenol A that are within about 5 % of values obtained using a fresh phenol stream [0134], that the method for the production of bisphenol A comprises contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter [0017], that the ketone is acetone [0109, 0110, 0112], that the bisphenol A can comprise any combination of components, purities, and properties described therein, including various aspects wherein any individual component, purity, and/or property, such as, for example, organic purity can be either included or excluded from the composition [0152], that thus, combinations wherein comprising any one or more components, purities, and/or properties, but excluding other components, purities, and/or properties recited therein are contemplated [0152], that the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], and that the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138], which optionally reads on wherein the process further comprises the additional step of (c) using at least a part of the phenol fraction obtained in step (b) as educt in step (a).
De Brouwer does not teach a specific embodiment wherein the process further comprises the additional step of (c) using at least a part of the phenol fraction obtained in step (b) as educt in step (a). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to separate the product of De Brouwer’s step of contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter in De Brouwer’s method into a fraction comprising De Brouwer’s p,p-bisphenol A and o,p-bisphenol A and into a fraction comprising De Brouwer’s phenol that is unreacted, De Brouwer’s ketone that is acetone that is unreacted, and De Brouwer’s impurities that comprise methyl benzofuran, and to use a recycled phenol stream comprising De Brouwer’s phenol that is unreacted with De Brouwer’s phenol in De Brouwer’s step of contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter in De Brouwer’s method. The proposed modification would read on wherein the process further comprises the additional step of (c) using at least a part of the phenol fraction obtained in step (b) as educt in step (a) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for purifying De Brouwer’s bisphenol A that is produced in De Brouwer’s method for the production of bisphenol A, and because it would have been beneficial for reusing unreacted phenol because De Brouwer teaches that when using a recycled phenol stream, the dimethyl thiazolidine catalyst system can provide levels of p,p-bisphenol A that are within about 10 %, within about 8 %, without about 6 %, within about 4 %, or within about 2 % of values obtained using a fresh phenol stream [0134], that when using a recycled phenol stream, the dimethyl thiazolidine catalyst system can provide levels of p,p-bisphenol A that are within about 5 % of values obtained using a fresh phenol stream [0134], that the method for the production of bisphenol A comprises contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter [0017], that the ketone is acetone [0109, 0110, 0112], that the bisphenol A can comprise any combination of components, purities, and properties described therein, including various aspects wherein any individual component, purity, and/or property, such as, for example, organic purity can be either included or excluded from the composition [0152], that thus, combinations wherein comprising any one or more components, purities, and/or properties, but excluding other components, purities, and/or properties recited therein are contemplated [0152], that the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], and that the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138].
Regarding claim 11, De Brouwer teaches that the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], that the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138], that bisphenol synthesized using the method can be useful in producing polycarbonate [0142], that bisphenol prepared from the method can produce a polycarbonate [0142], that bisphenol A produced using the method can result in polycarbonate materials [0145], and that polycarbonate is produced from bisphenol A prepared by the method [0145], which reads on a process for preparing polycarbonate comprising the steps of (i) obtaining a ortho,para-, and/or para,para-bisphenol A according to the process of claim 1, and (ii) polymerizing the ortho,para-, and/or para,para-bisphenol A obtained in step (i) as claimed.
Regarding claim 12, De Brouwer teaches that the bisphenol A and polycarbonate can comprise any combination of components, purities, and properties described therein, including various aspects wherein any individual component, purity, and/or property, such as, for example, organic purity can be either included or excluded from the composition [0152], that thus, combinations wherein comprising any one or more components, purities, and/or properties, but excluding other components, purities, and/or properties recited therein are contemplated [0152], that the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138], that bisphenol synthesized using the method can be useful in producing polycarbonate [0142], that bisphenol prepared from the method can produce a polycarbonate [0142], that bisphenol A produced using the method can result in polycarbonate materials [0145], and that polycarbonate is produced from bisphenol A prepared by the method [0145], which optionally reads on wherein the process of step (i) further comprises a step of purifying the ortho,para-, and/or para,para-bisphenol A in order to reduce the amount of at least one impurity formed due to the presence of 2-methyl benzofuran in step (a) as claimed.
De Brouwer does not teach a specific embodiment wherein the process of step (i) further comprises a step of purifying the ortho,para-, ortho,ortho-, and/or para,para-bisphenol A in order to reduce the amount of at least one impurity formed due to the presence of 2-methyl benzofuran in step (a). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of purifying De Brouwer’s bisphenol A by excluding De Brouwer’s impurity that comprises methyl benzofuran and any product thereof from De Brouwer’s bisphenol A before De Brouwer’s step of producing polycarbonate from De Brouwer’s bisphenol A that comprises p,p-bisphenol A and o,p-bisphenol A in De Brouwer’s method. The proposed modification would read on wherein the process of step (i) further comprises a step of purifying the ortho,para-, and/or para,para-bisphenol A in order to reduce the amount of at least one impurity formed due to the presence of 2-methyl benzofuran in step (a) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for purifying De Brouwer’s bisphenol A, and for obtaining a polycarbonate that is more pure because De Brouwer teaches that the bisphenol A and polycarbonate can comprise any combination of components, purities, and properties described therein, including various aspects wherein any individual component, purity, and/or property, such as, for example, organic purity can be either included or excluded from the composition [0152], that thus, combinations wherein comprising any one or more components, purities, and/or properties, but excluding other components, purities, and/or properties recited therein are contemplated [0152], that the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138], that bisphenol synthesized using the method can be useful in producing polycarbonate [0142], that bisphenol prepared from the method can produce a polycarbonate [0142], that bisphenol A produced using the method can result in polycarbonate materials [0145], and that polycarbonate is produced from bisphenol A prepared by the method [0145].
Regarding claim 13, De Brouwer teaches that the dimethyl thiazolidine is a promoter [0120], that in one aspect, at least a portion of the promoter is ionically bound to the available acid sites of the ion exchange resin [0125], that in another aspect, at least a portion of the promoter is covalently bound to at least a portion of the ion exchange resin [0125], that in still another aspect, all or substantially all of the promoter is at least covalently bound to the ion exchange resin [0125], that in yet another aspect, the degree of attachment or binding between a promoter and an ion exchange resin can vary, such as, for example, covalent binding, ionic binding, and/or other interactions or attraction forces [0125], and that the promoter is not intended to be limited to any particular degree of attachment [0125], which means that optionally, at least a portion of De Brouwer’s dimethyl thiazolidine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin, which optionally reads on wherein at least 75 mol% of the sulfur containing cocatalyst of the catalyst system is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a).
D Brouwer does not teach a specific embodiment wherein at least 75 mol% of the sulfur containing cocatalyst of the catalyst system is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a). Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select De Brouwer’s dimethyl thiazolindine and De Brouwer’s ion exchange resin in De Brouwer’s method, such that at least three-fourths of De Brouwer’s dimethyl thiazolindine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin. The proposed modification would read on wherein at least 75 mol% of the sulfur containing cocatalyst of the catalyst system is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been obvious to try with a reasonable expectation of success because De Brouwer teaches that the dimethyl thiazolidine is a promoter [0120], that in one aspect, at least a portion of the promoter is ionically bound to the available acid sites of the ion exchange resin [0125], that in another aspect, at least a portion of the promoter is covalently bound to at least a portion of the ion exchange resin [0125], that in still another aspect, all or substantially all of the promoter is at least covalently bound to the ion exchange resin [0125], that in yet another aspect, the degree of attachment or binding between a promoter and an ion exchange resin can vary, such as, for example, covalent binding, ionic binding, and/or other interactions or attraction forces [0125], and that the promoter is not intended to be limited to any particular degree of attachment [0125], which means that optionally, at least a portion of De Brouwer’s dimethyl thiazolidine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin. 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 15, De Brouwer teaches that the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], that the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138], that the bisphenol A prepared by the method can be used to produce polycarbonate copolymer materials, for example a polyester-polycarbonate copolymer, a polysiloxane-polycarbonate copolymer, an alkylene terephthalate-polycarbonate copolymer, or a combination thereof [0151], and that the bisphenol A prepared by the method can be used to produce other polycarbonate copolymers not specifically recited therein [0151], which reads on wherein step (ii) is performed in the presence of at least one further monomer in order to obtain a polycarbonate as claimed.
Claims 1-9 and 11-15 are rejected under 35 U.S.C. 103 as being unpatentable over Carvill et al. (US 2005/0004406 A1) in view of De Brouwer et al. (WO 2012/150560 A1, cited in IDS, made of record on 06/29/2023).
Regarding claims 1, 9, and 13, Carvill teaches a process for the reaction of a ketone with a phenol to form a bisphenol comprising reacting a feed comprising a phenol, a ketone, and water in the presence of an ion exchange resin catalyst to produce an effluent, determining the para-para bisphenol selectivity of the reaction, and adjusting the concentration of the water in the feed based upon the para-para bisphenol selectivity [0007], wherein the catalyst is selective for the production of a single isomer that is para-para bisphenol, or some para-para bisphenol is isomerized to ortho-para bisphenol [0016], wherein the phenol starting materials may be commercial grade or better [0030], wherein as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0030], wherein the ketone is acetone, the phenol is phenol, and the bisphenol is bisphenol A [0034, 0037], wherein the ion exchange catalyst is used in combination with a bulk promoter that is a cycloaliphatic thiol, an alkyl thiol, an aromatic thiol, an aliphatic thiol, thioglycolic acid, or 3-mercaptopropionic acid [0052], which reads on a process for preparing ortho,para and/or para,para-bisphenol A comprising the step of (a) condensing raw phenol and raw acetone in the presence of a catalyst system, wherein the catalyst system comprises an ion exchange resin catalyst and a sulfur containing cocatalyst, wherein at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a), wherein the amount of 2-methyl benzofuran present in step (a) is 0 or higher than 0 ppm with respect to the total weight of the raw phenol, wherein optionally the 2-methyl benzofuran present in step (a) is introduced into the process step (a) as impurity in the raw phenol, wherein 100 mol% of the sulphur containing cocatalyst of the catalyst system is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a).
Carvill does not teach that the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol, and does not teach a specific embodiment wherein the 2-methyl benzofuran present in step (a) is introduced into the process step (a) as impurity in the raw phenol. However, De Brouwer teaches a method for the production of bisphenol A comprising contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter, wherein the method does not comprises a pretreatment and/purification step for the phenol and ketone [0017], wherein the ketone is acetone [0109, 0110, 0112], wherein the phenol starting materials can be commercial grade or better [0107], wherein as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], where in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], wherein these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], wherein the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], wherein the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138]. Carvill and De Brouwer are analogous art because both references are in the same field of endeavor of a process for preparing ortho,para- or para,para-bisphenol A comprising the step of condensing raw phenol and raw acetone in the presence of a catalyst system comprising an ion exchange resin catalyst and a sulfur containing cocatalyst. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the level of methyl benzofuran in Carvill’s phenol in Carvill’s process to be greater than 1 ppm with respect to the weight of Carvill’s phenol, as suggested by De Brouwer. The proposed modification would read on wherein the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol as claimed, wherein the 2-methyl benzofuran present in step (a) is introduced into the process step (a) as impurity in the raw phenol as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing the lifetime of Carvill’s ion exchange resin catalyst in combination with Carvill’s bulk promoter, and for optimizing the reaction rates in Carvill’s process because De Brouwer teaches that in a method for the production of bisphenol A comprising contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter, the method does not comprises a pretreatment and/purification step for the phenol and ketone [0017], the ketone is acetone [0109, 0110, 0112], the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], that these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], and that these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], and because Carvill teaches that the phenol starting materials may be commercial grade or better [0030], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0030], and that the process for the reaction of a ketone with a phenol to form a bisphenol comprises reacting a feed comprising a phenol, a ketone, and water in the presence of an ion exchange resin catalyst to produce an effluent [0007], which means that the level of methyl benzofuran in Carvill’s phenol in Carvill’s process in ppm with respect to the weight of Carvill’s phenol would have affected the lifetime of Carvill’s ion exchange resin catalyst in combination with Carvill’s bulk promoter, and the reaction rates in Carvill’s process.
Regarding claim 2, Carvill teaches that the phenol starting materials may be commercial grade or better [0030], and that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0030], which read on wherein the amount of 2-methyl benzofuran present in step (a) is 0 or higher than 0 ppm with respect to the total weight of the raw phenol.
Carvill does not teach that the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm and equal to or lower than 5000 ppm with respect to the total weight of the raw phenol. However, De Brouwer teaches a method for the production of bisphenol A comprising contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter, wherein the method does not comprises a pretreatment and/purification step for the phenol and ketone [0017], wherein the ketone is acetone [0109, 0110, 0112], wherein the phenol starting materials can be commercial grade or better [0107], wherein as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], where in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], wherein these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], wherein the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], wherein the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138]. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the level of methyl benzofuran in Carvill’s phenol in Carvill’s process to be greater than 1 ppm and less than or equal to 5000 ppm with respect to the weight of Carvill’s phenol. The proposed modification would read on wherein the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm and equal to or lower than 5000 ppm with respect to the total weight of the raw phenol as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing the lifetime of Carvill’s ion exchange resin catalyst in combination with Carvill’s bulk promoter, and for optimizing the reaction rates in Carvill’s process because De Brouwer teaches that in a method for the production of bisphenol A comprising contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter, the method does not comprises a pretreatment and/purification step for the phenol and ketone [0017], the ketone is acetone [0109, 0110, 0112], the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], that these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], and that these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], and because Carvill teaches that the phenol starting materials may be commercial grade or better [0030], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0030], and that the process for the reaction of a ketone with a phenol to form a bisphenol comprises reacting a feed comprising a phenol, a ketone, and water in the presence of an ion exchange resin catalyst to produce an effluent [0007], which means that the level of methyl benzofuran in Carvill’s phenol in Carvill’s process in ppm with respect to the weight of Carvill’s phenol would have affected the lifetime of Carvill’s ion exchange resin catalyst in combination with Carvill’s bulk promoter, and the reaction rates in Carvill’s process.
Regarding claim 3, Carvill teaches that the phenol starting materials may be commercial grade or better [0030], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0030], that some of the p,p-bisphenol may be isomerized to o,p-bisphenol, thereby reducing the selectivity of the reaction and the purity of the reactor effluent [0016], that water added at the beginning of a catalyst’s lifetime will suppress isomerization reactions and will increase p,p-bisphenol selectivity and therefore p,p-bisphenol purity [0017], that the high overall selectivity when combined with the high p/p:o/p ratio indicates that little or no impurity aside from o/p bisphenol is produced [0022], that the high degree of selectivity of the reaction for p/p bisphenol results in the amount of impurities being greatly reduced, thus facilitating the isolation of the p/p bisphenol, improving the overall efficiency of the reaction and isolation, lengthening the life of the catalyst, as well as reducing the cost of the production of p/p bisphenol [0061], that the feed may also contain low levels of bisphenol and impurities resulting from the manufacture of bisphenol [0057], that the residual phenol and other starting materials are typically isolated before being recycled to the reaction feed but small amounts of impurities can remain and thus become part of the feed [0057], that passing the feed through the modified ion exchange resin catalyst results in an effluent comprising bisphenol, residual starting materials, water produced in the reaction, and side products [0060], and that the bisphenol may then be isolated from the residual starting materials, water, and side products found in the effluent [0061]. As explained above for claim 1, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the level of methyl benzofuran in Carvill’s phenol in Carvill’s process to be greater than 1 ppm with respect to the weight of Carvill’s phenol, as suggested by De Brouwer. Therefore, Carvill in De Brouwer renders it obvious wherein step (a) is conducted in the additional presence of at least one impurity formed due to the presence of 2-methyl benzofuran in step (a).
Regarding claim 4, Carvill teaches that the phenol starting materials may be commercial grade or better [0030], and that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0030]. As explained above for claim 1, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the level of methyl benzofuran in Carvill’s phenol in Carvill’s process to be greater than 1 ppm with respect to the weight of Carvill’s phenol, as suggested by De Brouwer. Therefore, Carvill in De Brouwer renders it obvious wherein the 2-methyl benzofuran is present throughout the whole process step (a) as claimed.
Regarding claim 5, Carvill teaches that the process for the reaction of a ketone with a phenol to form a bisphenol comprises reacting a feed comprising a phenol, a ketone, and water in the presence of an ion exchange resin catalyst to produce an effluent [0007], that the catalyst is selective for the production of a single isomer that is para-para bisphenol, or some para-para bisphenol is isomerized to ortho-para bisphenol [0016], that passing the feed through the modified ion exchange resin catalyst results in an effluent comprising bisphenol, residual starting materials, water produced in the reaction, and side products [0060], and that the bisphenol may then be isolated from the residual starting materials, water, and side products found in the effluent [0061]. As explained above for claim 1, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the level of methyl benzofuran in Carvill’s phenol in Carvill’s process to be greater than 1 ppm with respect to the weight of Carvill’s phenol, as suggested by De Brouwer. Therefore, Carvill in view of De Brouwer renders it obvious wherein the process further comprises the following step: (b) separating the mixture obtained after step (a) into a bisphenol A fraction comprising at least one of ortho,para- or para,para-bisphenol A and a phenol fraction, wherein the phenol fraction comprises unreacted phenol and at least one impurity formed due to the presence of 2-methyl benzofuran in step (a) as claimed.
Regarding claim 6, Carvill teaches that the bisphenol may then be isolated from the residual starting materials, water, and side products found in the effluent [0061], that the p/p bisphenol may be isolated from the bisphenol containing product stream by adduct crystallization, solvent crystallization, melt crystallization, or a combination of the foregoing isolation methods [0061], which reads on wherein the separation in step (b) is performed using a crystallization technique as claimed.
Regarding claim 7, Carvill teaches that the process for the reaction of a ketone with a phenol to form a bisphenol comprises reacting a feed comprising a phenol, a ketone, and water in the presence of an ion exchange resin catalyst to produce an effluent [0007], that passing the feed through the modified ion exchange resin catalyst results in an effluent comprising bisphenol, residual starting materials, water produced in the reaction, and side products [0060], that the bisphenol may then be isolated from the residual starting materials, water, and side products found in the effluent [0061], that in the isolation process, water, residual ketone, and some residual phenol are removed first [0061], and that the removed ketone and residual phenol can be separated from the water and recycled to the reaction feed [0061], which reads on wherein the process further comprises the additional step of (c) using at least a part of the phenol fraction obtained in step (b) as educt in step (a) as claimed.
Regarding claim 8, Carvill teaches that the ion exchange catalyst is used in combination with a bulk promoter that is 3-mercaptopropionic acid [0052], which reads on wherein the sulfur containing cocatalyst is selected from mercaptopropionic acid as claimed.
Regarding claim 11, Carvill teaches a process for the manufacture of polycarbonate comprising producing an effluent comprising the bisphenol, reacting said bisphenol with a carbonic acid derivative or a carbonate diester in the presence of a polymerization catalyst [0008], which reads on a process for preparing polycarbonate comprising the steps of (i) obtaining a ortho,para- and/or para,para-bisphenol A according to the process of claim 1, and (ii) polymerizing the ortho,para and/or para,para-bisphenol A obtained in step (i) as claimed.
Regarding claim 12, Carvill teaches that the process for the reaction of a ketone with a phenol to form a bisphenol comprises reacting a feed comprising a phenol, a ketone, and water in the presence of an ion exchange resin catalyst to produce an effluent [0007], that the catalyst is selective for the production of a single isomer that is para-para bisphenol, or some para-para bisphenol is isomerized to ortho-para bisphenol [0016], that passing the feed through the modified ion exchange resin catalyst results in an effluent comprising bisphenol, residual starting materials, water produced in the reaction, and side products [0060], and that the bisphenol may then be isolated from the residual starting materials, water, and side products found in the effluent [0061]. As explained above for claim 1, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the level of methyl benzofuran in Carvill’s phenol in Carvill’s process to be greater than 1 ppm with respect to the weight of Carvill’s phenol, as suggested by De Brouwer. Therefore, Carvill in view of De Brouwer renders it obvious wherein the process of step (i) further comprises a step of purifying the ortho,para- and/or para,para-bisphenol A in order to reduce the amount of at least one impurity formed due to the presence of 2-methyl benzofuran in step (a) as claimed.
Regarding claim 14, Carvill in De Brouwer satisfies the limitation the process of claim 8, wherein the alkyl sulfide is ethyl sulfide as claimed because claims 8 and 14 do not require the sulfur containing cocatalyst to be selected from alkyl sulfides if the sulfur containing cocatalyst is selected from mercaptopropionic acid, and Carvill’s teachings read on the sulfur containing cocatalyst is selected from mercaptopropionic acid as claimed.
Regarding claim 15, Carvill teaches that the bisphenol may be used in the synthesis of polycarbonate [0062], that polycarbonate may be synthesized by interfacial polymerization methods [0062], that in interfacial polymerization, an aqueous solution of the bisphenol is combined with an organic solution containing an organic solvent and a carbonic acid derivative in the presence of a polymerization catalyst [0062], and that a polyfunctional compound, herein defined as having more than two functional groups, may also be present to function as a branching agent [0062], which reads on wherein step (ii) is performed in the presence of at least one further monomer in order to obtain a polycarbonate as claimed.
Claim 6 is rejected under 35 U.S.C. 103 as being unpatentable over De Brouwer et al. (WO 2012/150560 A1, cited in IDS, made of record on 06/29/2023) as applied to claim 5, and further in view of Carvill et al. (US 2004/0116751 A1).
Regarding claim 6, De Brouwer renders obvious the process according to claim 5 as explained above.
De Brouwer does not teach that the separation in step (b) is performed using a crystallization technique. However, Carvill teaches that p/p bisphenol may be isolated from the bisphenol containing product stream by adduct crystallization, solvent crystallization, melt crystallization, or a combination of the foregoing isolation methods [0061], that a commercial scale continuous process for the reaction of a ketone with a phenol to form a bisphenol comprises reacting a feed comprising a phenol and a ketone through a modified ion exchange resin catalyst [0004], that the resin is modified by neutralization of the acid sites with a mercapto promoter [0004], that an effluent from a commercial scale continuous reaction of a ketone with a phenol to forma bisphenol comprises phenol, para-para and ortho-para bisphenol [0014], that the ketone is acetone [0033], and that the phenol starting material may contain measurable levels of impurities such as methyl benzofuran [0031]. De Brouwer and Carvill are analogous art because both references are in the same field of endeavor of a process for preparing ortho,para- and/or para,para- bisphenol A comprising the step of condensing raw phenol and raw acetone in the presence of a catalyst system comprising an ion exchange resin catalyst and a sulfur containing catalyst. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use a step of isolating De Brouwer’s bisphenol A produced by De Brouwer’s step of contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter from De Brouwer’s phenol that is unreacted, De Brouwer’s ketone that is acetone that is unreacted, and De Brouwer’s impurities that comprise methyl benzofuran by adduct crystallization, solvent crystallization, melt crystallization, or a combination of the foregoing isolation methods, as suggested by Carvill. The proposed modification would read on wherein the separation in step (b) is performed using a crystallization technique as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for purifying De Brouwer’s bisphenol A that is produced in De Brouwer’s method for the production of bisphenol A and for providing an effective method of purifying De Brouwer’s bisphenol A because Carvill teaches that p/p bisphenol may be isolated from the bisphenol containing product stream by adduct crystallization, solvent crystallization, melt crystallization, or a combination of the foregoing isolation methods [0061], and that a commercial scale continuous process for the reaction of a ketone with a phenol to form a bisphenol comprises reacting a feed comprising a phenol and a ketone through a modified ion exchange resin catalyst [0004], and because De Brouwer teaches that the method for the production of bisphenol A comprises contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter [0017], that the ketone is acetone [0109, 0110, 0112], that the bisphenol A can comprise any combination of components, purities, and properties described therein, including various aspects wherein any individual component, purity, and/or property, such as, for example, organic purity can be either included or excluded from the composition [0152], that thus, combinations wherein comprising any one or more components, purities, and/or properties, but excluding other components, purities, and/or properties recited therein are contemplated [0152], that the condensation of phenol and acetone to form bisphenol A can yield multiple isomers of bisphenol A [0136], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], and that the dimethyl thiazolidine catalyst system can exhibit a higher p,p-bisphenol A to o,p-bisphenol A ratio than a conventional bulk promoter system [0138].
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over De Brouwer et al. (WO 2012/150560 A1, cited in IDS, made of record on 06/29/2023) as applied to claim 5, and further in view of Mahood (US 8,247,619 B2).
Regarding claim 10, De Brouwer renders obvious the process according to claim 9 as explained above.
De Brouwer does not teach that the raw phenol is bio-based. However, Mahood teaches a method for preparing bisphenol comprising combining phenol and acetone in the presence of a catalyst to form bisphenol A, wherein both the phenol and the acetone contain at least 0.5% of bioderived impurities, where in the case of bioderived phenol, these impurities may include 2-methylbenzofuran (2:15-19). De Brouwer and Mahood are analogous art because both references are in the same field of endeavor of a process for preparing bisphenol A comprising the step of condensing raw phenol and raw acetone in the presence of a catalyst system, wherein the amount of 2-methyl benzofuran present in step (a) is optionally higher than 0 ppm with respect to the total weight of the raw phenol. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Mahood’s phenol that contains at least 0.5% of bioderived impurities that are 2-methylbenzofuran to substitute for De Brouwer’s phenol in De Brouwer’s method. The proposed modification would read on wherein the raw phenol is bio-based as claimed. One of ordinary skill in the art would have been motivated to do so because Mahood teaches that a method for preparing bisphenol comprising combining phenol and acetone in the presence of a catalyst to form bisphenol A, wherein both the phenol and the acetone contain at least 0.5% of bioderived impurities, where in the case of bioderived phenol, these impurities may include 2-methylbenzofuran (2:15-19), is beneficial for having less fossil fuel-based carbon content and for production of polycarbonates with less fossil fuel-based carbon content (2:24-26), which would have been desirable for De Brouwer’s method because De Brouwer teaches that the method for the production of bisphenol A comprises contacting a phenol and a ketone in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter, wherein the method does not comprises a pretreatment and/purification step for the phenol and ketone [0017], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], and that bisphenol synthesized using the method can be useful in producing polycarbonate [0142].
Claim 10 is rejected under 35 U.S.C. 103 as being unpatentable over Carvill et al. (US 2005/0004406 A1) in view of De Brouwer et al. (WO 2012/150560 A1, cited in IDS, made of record on 06/29/2023) as applied to claim 9, and further in view of Mahood (US 8,247,619 B2).
Regarding claim 10, Carvill in view of De Brouwer renders obvious the process according to claim 9 as explained above.
Carvill does not teach that the raw phenol is bio-based. However, Mahood teaches a method for preparing bisphenol comprising combining phenol and acetone in the presence of a catalyst to form bisphenol A, wherein both the phenol and the acetone contain at least 0.5% of bioderived impurities, where in the case of bioderived phenol, these impurities may include 2-methylbenzofuran (2:15-19). Carvill and Mahood are analogous art because both references are in the same field of endeavor of a process for preparing bisphenol A comprising the step of condensing raw phenol and raw acetone in the presence of a catalyst system, wherein the amount of 2-methyl benzofuran present in step (a) is optionally higher than 0 ppm with respect to the total weight of the raw phenol. Before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to use Mahood’s phenol to substitute for Carvill’s phenol in Carvill’s process. The proposed modification would read on wherein the raw phenol is bio-based as claimed. One of ordinary skill in the art would have been motivated to do so because Mahood teaches that a method for preparing bisphenol comprising combining phenol and acetone in the presence of a catalyst to form bisphenol A, wherein both the phenol and the acetone contain at least 0.5% of bioderived impurities, where in the case of bioderived phenol, these impurities may include 2-methylbenzofuran (2:15-19), is beneficial for having less fossil fuel-based carbon content and for production of polycarbonates with less fossil fuel-based carbon content (2:24-26), which would have been desirable for Carvill’s process because Carvill teaches that the process for the reaction of a ketone with a phenol to form a bisphenol comprises reacting a feed comprising a phenol, a ketone, and water in the presence of an ion exchange resin catalyst to produce an effluent [0007], that the phenol starting materials may be commercial grade or better [0030], that a process for the manufacture of polycarbonate comprises producing an effluent comprising the bisphenol, and reacting said bisphenol with a carbonic acid derivative or a carbonate diester in the presence of a polymerization catalyst [0008].
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).
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Claims 1-9 and 11-15 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-9 and 11-17 of U.S. Patent No. 12/662,442 B2. Although the claims at issue are not identical, they are not patentably distinct from each other because the patent claims a process for preparing ortho,para-, ortho,ortho- and/or para,para- bisphenol A comprising the step of (a) condensing raw phenol and raw acetone in the presence of a catalyst system, wherein the catalyst system comprises an ion exchange resin catalyst and a sulfur containing cocatalyst, wherein at least part, of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a), wherein at least two of the following (A) to (F) are true:(A) the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol; (B) the amount of hydroxyacetone present in step (a) is higher than 1 ppm with respect to the total weight of the sum of the weights of the raw phenol and the raw acetone; (C) the amount of alpha-methylstyrene present in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol; (D) the amount of acetophenone present in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol; (E) the amount of benzene present in step (a) is higher than 1 ppm with respect to the total weight of the raw acetone; and/or (F) the amount of cumene present in step (a) is higher than 1 ppm with respect to the total weight of the raw acetone (claim 1), which reads on a process for preparing ortho,para-, ortho,ortho- and/or para,para- bisphenol A comprising the step of (a) condensing raw phenol and raw acetone in the presence of a catalyst system, wherein the catalyst system comprises an ion exchange resin catalyst and a sulfur containing cocatalyst, wherein at least part, of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a),characterized in that wherein the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol as claimed.
Response to Arguments
Applicant's arguments filed 06/01/2026 have been fully considered but they are not persuasive. In response to the applicant’s argument that Applicant respectfully requests the Office to remove the provisional rejection of claims 1-9 and 11-15 on the ground of nonstatutory double patenting as being unpatentable over claims 1-9 and 11-17 of copending Application No. 18/270,651 because the subject application does not require at least two impurities as required by claim 1 of the ‘651 Application (p. 6), the copending Application No. 18/270,651 issued as U.S. Patent No. 12/662,442 B2 on 06/23/2026, which was after the previous Office was mailed on 01/30/2026. Claims 1-9 and 11-15 are rejected on the ground of nonstatutory double patenting as being unpatentable over claims 1-9 and 11-17 of U.S. Patent No. 12/662,442 B2. Although claim 1 of the patent requires at least two impurities, one of the impurities is 2-methyl benzofuran in an amount in step (a) that is higher than 1 ppm with respect to the total weight of the raw phenol (claim 1), which reads on the amount of 2-methyl-benzofuran in step (a) that is recited in claim 1 of the instant application. Claims 1-9 and 11-15 of the instant application do not exclude other impurities from being present in step (a) as long as the amount of 2-methyl-benzofuran in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol.
Applicant’s arguments, see p. 7, filed 06/01/2026, with respect to the rejection of claim 12 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, have been fully considered and are persuasive. The rejection of claim 12 under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, has been withdrawn.
Applicant's arguments filed 06/01/2026 have been fully considered but they are not persuasive. In response to the applicant argument that it is beneficial for the system of De Brouwer to utilize an attached promoter catalyst (p. 8), claim 1 recites the limitation “at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a)”, which does not exclude the presence of a part of the sulfur containing cocatalyst that is covalently or ionically bound to the ion exchange resin catalyst at the beginning of process step (a) as long as at least part of the sulfur containing cocatalyst is neither nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a). De Brouwer renders obvious this limitation. Specifically, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select De Brouwer’s dimethyl thiazolindine and De Brouwer’s ion exchange resin in De Brouwer’s method, such that at least a portion of De Brouwer’s dimethyl thiazolindine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin. The proposed modification would read on wherein at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) as claimed. One of ordinary skill in the art would have been motivated to do so because it would have been obvious to try with a reasonable expectation of success because De Brouwer teaches that the dimethyl thiazolidine is a promoter [0120], that in one aspect, at least a portion of the promoter is ionically bound to the available acid sites of the ion exchange resin [0125], that in another aspect, at least a portion of the promoter is covalently bound to at least a portion of the ion exchange resin [0125], that in still another aspect, all or substantially all of the promoter is at least covalently bound to the ion exchange resin [0125], that in yet another aspect, the degree of attachment or binding between a promoter and an ion exchange resin can vary, such as, for example, covalent binding, ionic binding, and/or other interactions or attraction forces [0125], and that the promoter is not intended to be limited to any particular degree of attachment [0125], which means that optionally, at least a portion of De Brouwer’s dimethyl thiazolidine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin. 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)).
In response to the applicant’s argument that independent claim 1 of De Brouwer describes a bisphenol-A prepared by contacting a phenol and at least one of a ketone, an aldehyde, or a combination thereof in the presence of an attached ion exchange resin catalyst comprising a dimethyl thiazolidine promoter, and that De Brouwer therefore teaches away from at least part of the sulfur containing cocatalyst of the catalyst system being neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) (p. 8), the rejection of the claims that is set forth in this Office action is not based on De Brouwer’s claim 1. The rejection of claim 1 is based on De Brouwer’s broader disclosure. Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments (MPEP 2123(II)). The use of patents as references is not limited to what the patentees describe as their own inventions or to the problems with which they are concerned (MPEP 2123(I)). A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments (MPEP 2123(I)). De Brouwer does not teach away from the limitation in claim 1, and De Brouwer renders obvious at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) as claimed. Specifically, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to select De Brouwer’s dimethyl thiazolindine and De Brouwer’s ion exchange resin in De Brouwer’s method, such that at least a portion of De Brouwer’s dimethyl thiazolindine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin. One of ordinary skill in the art would have been motivated to do so because it would have been obvious to try with a reasonable expectation of success because De Brouwer teaches that the dimethyl thiazolidine is a promoter [0120], that in one aspect, at least a portion of the promoter is ionically bound to the available acid sites of the ion exchange resin [0125], that in another aspect, at least a portion of the promoter is covalently bound to at least a portion of the ion exchange resin [0125], that in still another aspect, all or substantially all of the promoter is at least covalently bound to the ion exchange resin [0125], that in yet another aspect, the degree of attachment or binding between a promoter and an ion exchange resin can vary, such as, for example, covalent binding, ionic binding, and/or other interactions or attraction forces [0125], and that the promoter is not intended to be limited to any particular degree of attachment [0125], which means that optionally, at least a portion of De Brouwer’s dimethyl thiazolidine is neither ionically bound nor covalently bound to De Brouwer’s ion exchange resin. 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)).
In response to the applicant’s argument that De Brouwer teaches that the use of 3-MPA as a bulk promoter would result in the production of less desirable isomers of BPA and require additional reaction steps, and that it is therefore unreasonable to assume that a person of ordinary skill in the art would utilize De Brouwer to arrive at the present claims, especially the limitation of wherein at least part of the sulfur=containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) (p. 9), the rejection of the claims this set forth for in this Office action is not based on using 3-MPA as a bulk promoter. The rejection is based on De Brouwer’s teaching of a dimethyl thiazolidine promoter [0017]. De Brouwer renders obvious the amount of 2-methyl benzofuran present in step (a) is higher than 1 ppm with respect to the total weight of the raw phenol as claimed. Specifically, before the effective filing date of the claimed invention, one of ordinary skill in the art would have found it obvious to optimize the amount of methyl benzofuran in De Brouwer’s phenol in De Brouwer’s method to be greater than 1 ppm with respect to the weight of De Brouwer’s phenol. One of ordinary skill in the art would have been motivated to do so because it would have been beneficial for optimizing the lifetime of De Bouwer’s catalyst system in De Bouwer’s method, and for optimizing the reaction rates in De Bouwer’s method because De Bouwer teaches that the method does not comprises a pretreatment and/purification step for the phenol and ketone [0017], that the phenol starting materials can be commercial grade or better [0107], that as readily understood by one of ordinary skill in the art commercial grade reagents may contain measurable levels of typical impurities such as methyl benzofuran [0107], that in the production of bisphenol A, phenol and acetone reactants can contain impurities [0099], that these impurities can deactivate the catalyst system, resulting in slower reaction rates and shorter catalyst lifetimes [0099], that the promoter catalyst system can tolerate impurities in reactant and/or recycle streams [0101], that the dimethyl thiazolidine attached promoter catalyst system can tolerate phenol and alcohol impurities without reducing the lifetime of the catalyst system [0127], and that the dimethyl thiazolidine attached promoter catalyst system can tolerate other impurities detrimental to conventional catalyst systems [0127], which means that the amount of methyl benzofuran in De Brouwer’s phenol in De Brouwer’s method in ppm with respect to the weight of De Brouwer’s phenol would have affected the lifetime of De Bouwer’s catalyst system in De Bouwer’s method, and the reaction rates in De Bouwer’s method.
In response to the applicant’s argument that Carvill uses a number of experimental examples that, in all cases, the ion exchange resin catalyst is modified with 4-pyridylethylmercaptan or mercaptoamine, and that the examples provided by the method of Carvill therefore would not motivate a person having ordinary skill in the art to use a catalyst system comprising an ion exchange resin catalyst and a sulfur containing cocatalyst, wherein at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) (p. 9-10), the rejection of the claims that is set forth in this Office action is not based on Carvill’s examples. The rejection is based on Carvill’s broader disclosure. Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments (MPEP 2123(II)). Carvill teaches a process for the reaction of a ketone with a phenol to form a bisphenol comprising reacting a feed comprising a phenol, a ketone, and water in the presence of an ion exchange resin catalyst to produce an effluent [0007], wherein the ion exchange catalyst is used in combination with a bulk promoter that is a cycloaliphatic thiol, an alkyl thiol, an aromatic thiol, an aliphatic thiol, thioglycolic acid, or 3-mercaptopropionic acid [0052], which reads on wherein at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) as claimed.
In response to the applicant’s argument that based on Carvill’s paragraph [0053], a person having ordinary skill in the art would not be motivated to utilize the process according to Carvill to arrive at the limitation of at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) (p. 10), the rejection of the claims that is set forth in this Office action is not based on Carvill’s paragraph [0053] and is not based on Carvill’s embodiment in which the ion exchange resin catalyst is used in combination with an attached promoter. The rejection is based on Carvill’s embodiment in which the ion exchange catalyst is used in combination with a bulk promoter that is a cycloaliphatic thiol, an alkyl thiol, an aromatic thiol, an aliphatic thiol, thioglycolic acid, or 3-mercaptopropionic acid [0052], which reads on at least part of the sulfur containing cocatalyst is neither covalently nor ionically bound to the ion exchange resin catalyst at the beginning of process step (a) as claimed. A reference may be relied upon for all that it would have reasonably suggested to one having ordinary skill in the art, including nonpreferred embodiments (MPEP 2123(I)). Disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments (MPEP 2123(II)).
In response to the applicant’s argument that dependent claims 2-15 are allowable at least because each such claim directly or indirectly depends from claim 1 (p. 10), claims 1-15 are not allowable because they are rejected under 35 U.S.C. 103 as being unpatentable over the references cited in the rejection that are set forth in this Office action.
Conclusion
THIS ACTION IS MADE FINAL. 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.
Correspondence
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/DAVID T KARST/Primary Examiner, Art Unit 1767
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