DETAILED ACTION
STATUS OF THE APPLICATION
Receipt is acknowledged of Applicants’ Amendments and Remarks, filed 24 July 2025, in the matter of Application No. 17/273,089. Said documents have been entered on the record. The Examiner further acknowledges the following:
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claims 1-2, 6-8, 11-12, and 14-17 are pending.
Claims 1, 6, and 14 has been amended.
Claims 5 and 13 have been cancelled.
Claims 16-17 have been newly added.
Thus, claims 1-2, 6-8, 11-12, and 14-17 represent all claims currently under consideration.
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 24 July 2025 has been entered.
Objections and/or Rejections and Response to Arguments
Rejections and/or objections not reiterated from previous office actions are hereby withdrawn. The following rejections and/or objections are either reiterated (Maintained Objections and/or Rejections) or newly applied (New Objections and/or Rejections, Necessitated by Amendment or New Objections and/or Rejections, NOT Necessitated by Amendment). They constitute the complete set presently being applied to the instant application.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1-2, 6-8, 11-12, and 14-17 are rejected under 35 U.S.C. 103 as being unpatentable over Palmer et al. (US 6,465,697 B1; PTO-892 of 03-29-2023), in view of Yoshitomi et al. (EP 2 019 089 A1; PTO-892 of 12-21-2021), and Iimuro et al. (EP 0 329 075 B1; PTO-892 of 03-29-2023) (partially newly applied as necessitated by amendment).
Regarding claims 1 and 16-17, Palmer et al. disclose a process for producing bisphenol-A comprising:
(a) reacting acetone and phenol in the presence of a catalyst system comprising an acidic heterogeneous catalyst and a catalyst promoter comprising at least one organic sulfur-containing compound to produce a reaction effluent comprising bisphenol-A, water, unreacted acetone, unreacted phenol and at least part of the catalyst promoter (column 2, lines 64 to column 5, line 45; column 7, lines 19-44).
(b) distilling at least part of the reaction effluent to remove water, catalyst promoter and unreacted acetone and a portion of the unreacted phenol, and leave a residual stream containing phenol, bisphenol A and catalyst promoter (column 7, lines 34-49 and column 10, lines 52-59);
and
(d) recovering bisphenol-A from the purified stream, wherein the recovering comprises crystallization to separate the purified stream into a solid bisphenol-A-containing product and a mother liquor stream (column 10, lines 52-64 and column 11, lines 1-8).
Palmer et al. further teaches that the particular dithioketal catalyst promoter compound chosen is preferably a type which, upon dissociation in the reaction zone, forms the same kind of carbonyl compound as the feed carbonyl compound chosen to make the polyphenol; in one embodiment, the feed carbonyl feed is acetone, and the dithioketal catalyst promoter composition comprises 2,2-bis(thiomethyl) propane, which in the presence of the acid catalyst, dissociates into acetone and a methyl mercaptan catalyst promoter (column 4, lines 62-67 and column 5, lines 1-3). Thus, the skilled artisan would recognize that Palmer teaches an unbound catalyst promoter, in a manner consistent with step (a) of instant claims 1 and 16, and that the in situ generated methyl mercaptan is an alkyl mercaptan that reads directly on the at least one organic sulfur-containing compound as recited in instant claims 16-17, respectively.
Palmer et al. differ from claims 1 and 16 in that Palmer et al. do not disclose the claimed distillation temperature of from 155 to 185°C and pressure of from 50 to 85 kPa, as recited in step (b) of the instant claims.
However, Palmer et al. disclose that the water, catalyst promoter, unreacted acetone and the unreacted phenol can be removed using any conventional method for separating materials with distillation being the simplest and most preferred method (column 7, lines 44-49).
Furthermore, Yoshitomi et al. disclose a process for producing high-purity bisphenol A (paragraph 0011). Subsequent to the condensation reaction step, Yoshitomi et al. disclose a concentration step comprising removing unreacted acetone, reaction product water and the like using vacuum distillation at a temperature of about 30 to 180 °C under a pressure of about 13 to 67 kPa (paragraph 0015).
One having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious that one could remove the water, catalyst promoter and unreacted acetone and a portion of the unreacted phenol from the crude polyphenol of Palmer et al., and leave a residual stream containing phenol, bisphenol A and less than 100 ppm by weight catalyst promoter by carrying out the distillation step of Palmer et al. using vacuum distillation, as taught by Yoshitomi et al., at temperature of about 30 to 180°C under a pressure of about 13 to 67 kPa, which overlaps with the claimed temperature and pressure range, since Palmer et al. disclose that the water, catalyst promoter, unreacted acetone and the unreacted phenol are removed from the crude polyphenol using distillation.
Palmer et al. further differ from claims 1 and 16 in that Palmer et al. do not disclose wherein the residual stream contains less than 10 ppm by weight of the catalyst promoter, less than 50 ppm by weight acetone, and less than 100 ppm by weight water, as recited in step (b) of the instant claims. However, one having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious to obtain the residual stream of Palmer et al. in view of Yoshitomi et al. and Iimuro et al. containing less than 10 ppm by weight of the catalyst promoter, less than 50 ppm by weight of acetone, and less than 100 ppm by weight water, since Palmer et al. desire that the dissociation products of the dithioketal catalyst promoter, excess water and unreacted carbonyl compounds are removed from the crude bisphenol A and Palmer et al. disclose that one can remove these compounds from the crude bisphenol-A using known distillation methods (column 7, lines 34-51), such as those taught by Yoshitomi et al., which utilizes temperatures and pressures that overlap with the claimed distillation temperatures and pressures (paragraph 0015). The ordinary skilled artisan would have had a reasonable expectation of success, since Palmer et al. in view of Yoshitomi et al. utilize distillation under the identical or substantially identical process conditions as the applicants. See MPEP 2112.01 I. In addition, Yoshitomi teaches a process for producing bisphenol A wherein free acid is removed in the presence of 0.01 to 1% by mass of water in the free-acid removing step (claim 9). The lower end of this range as taught by Yoshitomi corresponds to 100 ppm of water and is sufficiently close to the range recited in instant claim 1 as to render it obvious. MPEP § 2144.05(I) states that “a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.” Finally, regarding the claim 16 limitation less than 50 ppm by weight of water, one of ordinary skill could reasonably arrive at this water content based on the teachings of Palmer and Yoshitomi through means of routine experimentation. MPEP § 2144.05(II) states that “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.”
Palmer et al. further differ from claims 1 and 16 in that Palmer et al. do not disclose
(c) contacting the entire residual stream with a basic anion exchange resin to produce a purified stream, wherein the basic anion exchange resin is a weak-base anionic exchange resin containing primary, secondary or tertiary amine groups.
However, Palmer et al. disclose that the method of separation of the crude polyphenol is not limited and can include other well-known methods in combination with distillation (column 7, lines 34-51).
Furthermore, Iimuro et al. disclose that colorless and high-purity bisphenol A is required to be used as a raw material for polycarbonate resins, epoxy resins and engineering plastics (column 1, lines 6-9). Iimuro et al. disclose a process for producing colorless and high-purity bisphenol A by removing the acid catalyst from the product mixture comprising treating the product mixture with a specific weakly basic ion-exchange resin, and thereafter purifying the product mixture by the usual process (column 2, lines 28-35). The method comprises reacting phenol with acetone in the presence of a strongly acidic cation-exchange resin (column 2, lines 49-56). The reaction yields a product mixture containing bisphenol A, unreacted phenol, unreacted acetone, acid catalyst, water and by-products (paragraph bridging columns 2 and 3). The product mixture is distilled and the thus obtained liquid mixture containing bisphenol A, phenol, and a trace amount of acid is contacting with a weakly basic ion-exchange resin having pyridyl groups (a tertiary amine) as the exchange groups (column 3, lines 9-26). The treatment with the weakly basic ion-exchange resin may be carried at 70 to 150°C (column 3, lines 34-37).
Yoshitomi et al. disclose a process for producing high-purity bisphenol A with an excellent transparency (color) in particular by removing trace amount of free acid catalyst used in a reaction step and an isomerization catalyst used in an isomerization step (paragraph 0001, Examples 1-4 and claims 1, 3, 5, 7 and 9). Yoshitomi et al. disclose that bisphenol A that is a raw material of polycarbonate is required to be infinitely transparent (low color) (paragraph 0002). The method comprises reacting phenol with acetone in the presence of a strongly acidic cation-exchange resin (paragraph 0013). The reaction mixture from the condensation reaction is concentrated in two steps, which includes a vacuum distillation at a temperature of about 30 to 180°C and a pressure of about 13 to 67 kPa (paragraphs 0015 and 0027). The method also comprises a free-acid removal step that includes the use of a weak base ion exchange resin having primary to tertiary amine as a functional group (paragraphs 0019-0021). The temperature at which the weak base ion exchange resin is used is preferably from 40 to 100°C (paragraph 0020).
One having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious to carry out a step for removing acidic impurities after the distillation step in the process of Palmer et al. including the use of a weak-base anionic exchange resin containing primary, secondary or tertiary amine groups, as taught by Iimuro et al. and Yoshitomi et al., since Palmer et al. disclose that the method of separation of the crude polyphenol is not limited and can include other well-known methods in combination with distillation and both Iimuro et al. and Yoshitomi et al. have shown that a step for removing acidic impurities can be carried out after the distillation step in a process for producing high quality/purity bisphenol A using a weak-base anionic exchange resin containing primary, secondary or tertiary amine groups. The ordinary skilled artisan would have further been motivated to carry out a step for removing acidic impurities after the distillation step in the process of Palmer et al., as these treatments will provide a bisphenol A having transparency and high quality/purity useful as a raw material for polycarbonate resins, epoxy resins and engineering plastics.
Regarding claim 2, Palmer et al. in view of Yoshitomi et al. and Iimuro et al. disclose the process of claim 1, as described above, wherein the acidic heterogeneous catalyst comprises a sulfonated ion exchange resin (column 9, line 34 to column 10, line 21 and the Examples).
Regarding claim 6, Palmer et al. in view of Yoshitomi et al. and Iimuro et al. disclose the process of claim 1, as described above, and further comprising: (e) recycling at least part of the catalyst promoter removed in the distilling (b) to the reacting step (a), since Palmer et al. disclose that any fraction containing dissociation products, one of which is the mercaptan catalyst promoter, may be recycled back to the reaction zone or to any line or reactant feeding the reaction zone (column 7, lines 52-55).
Regarding claim 7, Palmer et al. in view of Yoshitomi et al. and Iimuro et al. disclose the process of claim 1, as described above, wherein the contacting (c) is conducted at a temperature of 70°C to 150°C (Iimuro et al.) or 40 to 100°C (Yoshitomi et al.), which encompasses or overlaps with the claimed range of from 80 to 120°C (Iimuro et al.- column 3, lines 34-37 and Yoshitomi et al.- paragraph 0020). It has been held that in the case where claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990); In re Geisler, 116 F.3d 1465, 1469-71, 43 USPQ2d 1362, 1365-66 (Fed. Cir. 1997).
Regarding claim 8, Palmer et al. in view of Yoshitomi et al. and Iimuro et al. disclose the process of claim 1, as described above, but do not expressly disclose wherein the contacting (c) is conducted by downward flow of the residual stream through a bed of basic anion exchange resin.
However, one having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious that the contacting of the residual stream through the bed of basic anion exchange resin in the process of Palmer et al. in view of Yoshitomi et al. and Iimuro et al. is conducted by downward flow, since the skilled artisan would have reasonably expected the reaction mixture to flow through the basic anion exchange resin downward with gravity. Furthermore, Palmer et al. teaches that the reactor can be oriented to produce an up-flow or down-flow stream (column 10, lines 46-51), such that the skilled artisan arrive at the limitation of the instant claim based on the teachings of Palmer alone.
Regarding claim 11, Palmer et al. in view of Yoshitomi et al. and Iimuro et al. disclose the process of claim 1, as described above. One having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious to (f) contact the mother liquor stream comprising other isomers of diphenylolpropane than bisphenol-A with a sulfonated acidic ion exchange catalyst under conditions to convert at least some of the other isomers of diphenylolpropane to bisphenol-A and produce an isomerized product stream, since Yoshitomi et al. disclose an isomerization step wherein the mother liquid is contacted with a sulfonic acid cation exchange resin to convert the 2,4’-isomer into bisphenol A (paragraphs 0016 and 0018).
Regarding claim 12, Palmer et al. in view of Yoshitomi et al. and Iimuro et al. disclose the process of claim 11, as described above. One having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious to (g) supply at least part of the isomerized product stream to the reacting step (a), since Yoshitomi et al. disclose that most of the isomerized liquid is returned to the condensation reaction step (paragraph 0018).
Regarding claim 14, Palmer et al. disclose a process for producing bisphenol-A comprising:
(a) reacting acetone and phenol in a molar ratio of phenol to acetone of at least 2:1 in the presence of a catalyst system comprising an acidic heterogeneous catalyst and an unbound catalyst promoter comprising at least one organic sulfur-containing compound to produce a reaction effluent comprising bisphenol-A, water, unreacted acetone, unreacted phenol and at least part of the unbound catalyst promoter (column 2, lines 64 to column 5, line 45; column 7, lines 19-44);
(b) distilling at least part of the reaction effluent produced in step (a) to remove water, unbound catalyst promoter, unreacted acetone and a portion of the unreacted phenol, and leave a residual stream containing phenol, bisphenol A, the unbound catalyst promoter, the water and the unreacted acetone (column 7, lines 34-49 and column 10, lines 52-59);
and
(d) recovering bisphenol-A from the purified stream, wherein the recovering comprises crystallization to separate the purified stream into a solid bisphenol-A-containing product and a mother liquor stream (column 10, lines 52-64 and column 11, lines 1-8).
Palmer et al. differ from claim 14 in that Palmer et al. do not disclose the claimed distillation temperature of from 155 to 185°C, pressure of from 50 to 85 kPa and leaving a residual stream containing less than 10 ppm by weight of the unbound catalyst promoter, less than 100 ppm by weight of water and less than 50 ppm by weight of acetone.
However, Palmer et al. disclose that the water, catalyst promoter, unreacted acetone and the unreacted phenol can be removed using any conventional method for separating materials with distillation being the simplest and most preferred method (column 7, lines 44-49).
Yoshitomi et al. disclose a process for producing high-purity bisphenol A (paragraph 0011). Subsequent to the condensation reaction step, Yoshitomi et al. disclose a concentration step comprising removing unreacted acetone, reaction product water and the like using vacuum distillation at a temperature of about 30 to 180°C under a pressure of about 13 to 67 kPa (paragraph 0015).
One having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious that one could remove the water, catalyst promoter and unreacted acetone and a portion of the unreacted phenol from the crude polyphenol of Palmer et al. and leave a residual stream containing phenol, bisphenol A and less than 10 ppm by weight of the unbound catalyst promoter, less than 100 ppm weight of water and less than 50 ppm by weight of acetone by carrying out the distillation step of Palmer et al. using vacuum distillation, as taught by Yoshitomi et al., at temperature of about 30 to 180°C under a pressure of about 13 to 67 kPa, which overlaps with the claimed temperature and pressure range, since Palmer et al. disclose that the water, catalyst promoter, unreacted acetone and the unreacted phenol are removed from the crude polyphenol using distillation. The ordinary skilled artisan would have a reasonable expectation that, since Palmer et al. in view of Yoshitomi et al. utilize distillation under the identical or substantially identical process conditions as the applicants that Palmer et al. in view of Yoshitomi et al. will inherently obtain a residual stream containing phenol, bisphenol A and less than 10 ppm by weight of the unbound catalyst promoter, less than 100 ppm weight of water and less than 50 ppm by weight of acetone. See MPEP 2112.01 I. Finally, Yoshitomi teaches a process for producing bisphenol A wherein free acid is removed in the presence of 0.01 to 1% by mass of water in the free-acid removing step (claim 9). The lower end of this range as taught by Yoshitomi corresponds to 100 ppm of water. MPEP § 2144.05(I) states that “a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.”
Palmer et al. further differ from claim 14 in that Palmer et al. do not disclose
(c) contacting the entire residual stream with a basic anion exchange resin to produce a purified stream, wherein the basic anion exchange resin is a weak-base anionic exchange resin containing primary, secondary or tertiary amine groups.
However, Palmer et al. disclose that the method of separation of the crude polyphenol is not limited and can include other well-known methods in combination with distillation (column 7, lines 34-51).
Yoshitomi et al. disclose a process for producing high-purity bisphenol A with an excellent transparency (color) in particular by removing trace amount of free acid catalyst used in a reaction step and an isomerization catalyst used in an isomerization step (paragraph 0001, Examples 1-4 and claims 1, 3, 5, 7 and 9). Yoshitomi et al. disclose that bisphenol A that is a raw material of polycarbonate is required to be infinitely transparent (low color) (paragraph 0002). The method comprises reacting phenol with acetone in the presence of a strongly acidic cation-exchange resin (paragraph 0013). The reaction mixture from the condensation reaction is concentrated in two steps, which includes a vacuum distillation at a temperature of about 30 to 180°C and a pressure of about 13 to 67 kPa (paragraphs 0015 and 0027). The method also comprises a free-acid removal step that includes the use of a weak base ion exchange resin having primary to tertiary amine as a functional group (paragraphs 0019-0021). The temperature at which the weak base ion exchange resin is used is preferably from 40 to 100°C (paragraph 0020).
Iimuro et al. disclose that colorless and high-purity bisphenol A is required to be used as a raw material for polycarbonate resins, epoxy resins and engineering plastics (column 1, lines 6-9). Iimuro et al. disclose a process for producing colorless and high-purity bisphenol A by removing the acid catalyst from the product mixture comprising treating the product mixture with a specific weakly basic ion-exchange resin, and thereafter purifying the product mixture by the usual process (column 2, lines 28-35). The method comprises reacting phenol with acetone in the presence of a strongly acidic cation-exchange resin (column 2, lines 49-56). The reaction yields a product mixture containing bisphenol A, unreacted phenol, unreacted acetone, acid catalyst, water and by-products (paragraph bridging columns 2 and 3). The product mixture is distilled and the thus obtained liquid mixture containing bisphenol A, phenol, and a trace amount of acid is contacting with a weakly basic ion-exchange resin having pyridyl groups (a tertiary amine) as the exchange groups (column 3, lines 9-26). The treatment with the weakly basic ion-exchange resin may be carried at 70 to 150°C (column 3, lines 34-37).
One having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious to carry out a step for removing acidic impurities after the distillation step in the process of Palmer et al. including the use of a weak-base anionic exchange resin containing primary, secondary or tertiary amine groups, as taught by Yoshitomi et al. and Iimuro et al., since Palmer et al. disclose that the method of separation of the crude polyphenol is not limited and can include other well-known methods in combination with distillation and both Yoshitomi et al. and Iimuro et al. have shown that a step for removing acidic impurities can be carried out after the distillation step in a process for producing high quality/purity bisphenol A using a weak-base anionic exchange resin containing primary, secondary or tertiary amine groups. The ordinary skilled artisan would have further been motivated to carry out a step for removing acidic impurities after the distillation step in the process of Palmer et al., as these treatments will provide a bisphenol A having transparency and high quality/purity useful as a raw material for polycarbonate resins, epoxy resins and engineering plastics.
Regarding the claim limitation (e) recycling at least part of the unbound catalyst promoter removed in the distilling (b) to the reacting step (a), as recited in instant claim 14, Palmer et al. in view of Yoshitomi et al. and Iimuro et al. disclose a process further comprising: (e) recycling at least part of the catalyst promoter removed in the distilling (b) to the reacting step (a), since Palmer et al. disclose that any fraction containing dissociation products, one of which is the mercaptan catalyst promoter, may be recycled back to the reaction zone or to any line or reactant feeding the reaction zone (column 7, lines 52-55).
Regarding the claim limitation wherein the mother liquor stream comprises other isomers of diphenylolpropane than bisphenol-A; and (f) contacting the mother liquor with a sulfonated acidic ion exchange catalyst under conditions to convert at least some of the other isomers of diphenylolpropane to bisphenol-A and produce an isomerized product stream, as recited in instant claim 14, one having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious to (f) contact the mother liquor stream comprising other isomers of diphenylolpropane than bisphenol-A with a sulfonated acidic ion exchange catalyst under conditions to convert at least some of the other isomers of diphenylolpropane to bisphenol-A and produce an isomerized product stream, since Yoshitomi et al. disclose an isomerization step wherein the mother liquid is contacted with a sulfonic acid cation exchange resin to convert the 2,4’-isomer into bisphenol A (paragraphs 0016 and 0018).
Regarding the claim limitation, (g) supplying at least part of the isomerized product stream to the reacting step (a), as recited in instant claim 14, one having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious to (g) supply at least part of the isomerized product stream to the reacting step (a), since Yoshitomi et al. disclose that most of the isomerized liquid is returned to the condensation reaction step (paragraph 0018).
Regarding claim 15, Palmer et al. in view of Yoshitomi et al. and Iimuro et al. disclose the process of claim 14, as described above, wherein the contacting (c) is conducted at a temperature of 70°C to 150°C (Iimuro et al.) or 40 to 100°C (Yoshitomi et al.), which encompasses or overlaps with the claimed range of from 90 to 120°C (Iimuro et al.- column 3, lines 34-37 and Yoshitomi et al.- paragraph 0020). It has been held that in the case where claimed ranges “overlap or lie inside ranges disclosed by the prior art” a prima facie case of obviousness exists. In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976); In re Woodruff, 919 F.2d 1575, 16 USPQ2d 1934 (Fed. Cir. 1990); In re Geisler, 116 F.3d 1465, 1469-71, 43 USPQ2d 1362, 1365-66 (Fed. Cir. 1997).
Response to Arguments
Claim Rejections - 35 USC § 103
Applicant's arguments filed 24 July 2025, asserting that the cited prior art does not (i) motivate one skilled in the art to modify Palmer with the conditions of the distillation step of Yoshitomi or (ii) teach the claimed composition of the residual stream with the low concentration of water, have been fully considered but they are not persuasive.
Applicant recites components of amended claims 1 and 14 and newly added claim 16, and argues the following:
“Applicant submits that Palmer in view of Patrascu, Yoshitomi, and Iimuro fails to disclose or teach the claimed conditions of the step (b) and the composition of the residual stream.
Palmer discloses a reaction between acetone and phenol in the presence of a catalyst and an unbound catalyst promoter (step (a)) to produce bisphenol-A optionally followed by distillation to reduce the concentration of unreacted acetone, unreacted phenol, the catalyst promoter, and excess water. Palmer at col. 7, 11. 34-51. However, Palmer is silent on the composition of the residue stream after distillation. Palmer immediately follows distillation with recovering the polyphenolic compound (e.g., bisphenol-A) with another separation technique, which is conventionally crystallization to separate polyphenol from a mother liquor. Palmer at col. 10, 11. 59-67. Accordingly, Palmer does not disclose or teach the conditions of step (b), the composition of the residual stream, or the inclusion of step (c).
Applicant submits that none of the other cited art discloses or teaches the composition of the residue stream after distillation. Rather, Patrasu is directed to excluding a distillation step between the reaction and crystallization. Patrasu at Abstract, col. 3, 11. 39-43, and FIG. 1. Further, Iimuro, in conjunction with a strongly acidic cation-exchange resin catalyst in the reaction step, discloses distillation at 70°C to 120°C and 50 mm Hg to 300 mmHg (6.7 kPa to 40.0 kPa), neither of which overlap with the claimed conditions. Iimuro at col. 3, 11. 24-32.”
This argument has been fully considered, but is not found to be persuasive. According to the new 103 rejections above, although Palmer does not explicitly teach the composition of the residue stream, as stated by Applicant, Palmer does disclose that the water, catalyst promoter, unreacted acetone, and the unreacted phenol can be removed by any conventional method for separating materials with distillation being the simplest and most preferred method (Palmer; Col. 7, lines 44-49). Furthermore, Yoshitomi et al. disclose a concentration step comprising removing unreacted acetone, reaction product water and the like using vacuum distillation at a temperature of about 30 to 180°C under a pressure of about 13 to 67 kPa (paragraph 0015). Thus, the skilled artisan would have found it obvious that one could remove the water, catalyst promoter and unreacted acetone and a portion of the unreacted phenol from the crude polyphenol of Palmer et al. and leave a residual stream containing phenol, bisphenol A and less than 10 ppm by weight of the unbound catalyst promoter, less than 100 ppm weight of water and less than 50 ppm by weight of acetone by carrying out the distillation step of Palmer et al. using vacuum distillation, as taught by Yoshitomi et al., at temperature of about 30 to 180°C under a pressure of about 13 to 67 kPa, which overlaps with the claimed temperature and pressure range, since Palmer et al. disclose that the water, catalyst promoter, unreacted acetone and the unreacted phenol are removed from the crude polyphenol using distillation. MPEP § 2144.01 states that “[I]n considering the disclosure of a reference, it is proper to take into account not only specific teachings of the reference but also the inferences which one skilled in the art would reasonably be expected to draw therefrom.” In addition, since Palmer et al. in view of Yoshitomi et al. utilize distillation under the identical or substantially identical process conditions as the applicants that Palmer et al. in view of Yoshitomi et al. will inherently obtain a residual stream containing phenol, bisphenol A and less than 10 ppm by weight of the unbound catalyst promoter, less than 100 ppm weight of water and less than 50 ppm by weight of acetone. See MPEP § 21112.01(I). Finally, although Palmer does not teach the inclusion of step (c), as stated by Applicant, however this deficiency is adequately addressed by Iimuro et al., who disclose a process for producing colorless and high-purity bisphenol A by removing the acid catalyst from the product mixture comprising treating the product mixture with a specific weakly basic ion-exchange resin, and thereafter purifying the product mixture by the usual process (column 2, lines 28-35); the method comprises reacting phenol with acetone in the presence of a strongly acidic cation-exchange resin (column 2, lines 49-56); and the product mixture is distilled and the thus obtained liquid mixture containing bisphenol A, phenol, and a trace amount of acid is contacting with a weakly basic ion-exchange resin having pyridyl groups (a tertiary amine) as the exchange groups (column 3, lines 9-26). Furthermore, Yoshitomi et al. teaches a method of bisphenol A production that comprises a free-acid removal step that includes the use of a weak base ion exchange resin having primary to tertiary amine as a functional group (paragraphs 0019-0021). Given the closely overlapping technical fields of bisphenol A manufacturing and purification, as taught by the cited prior art and consistent with the instantly claimed invention, the skilled artisan would have been sufficiently motivated to implement the inclusion of step (c) as taught by Iimuro and Yoshitomi to the method of Palmer to realize the predictable results of removing acidic impurities after the distillation step in a process for producing high quality/purity bisphenol A using a weak-base anionic exchange resin containing primary, secondary or tertiary amine groups, as detailed above. Therefore, the new claim rejections are maintained for the reasons of record and the reasons set forth above.
Applicant argues the following:
“The Office Action relies on Yoshitomi for allegedly teaching the conditions of step (b) and states that "[o]ne having ordinary skill in the art before the effective filing date of the claimed invention would have found it obvious that one could remove the water, catalyst promoter and unreacted acetone and a portion of the unreacted phenol from the crude polyphenol of Palmer et al., and leave a residual stream containing phenol, bisphenol A and less than 100 ppm by weight catalyst promoter by carrying out the distillation step of Palmer et al. using vacuum distillation, as taught by Yoshitomi et al., at temperature of about 30 to 180°C under a pressure of about 13 to 67 kPa, which overlaps with the claimed temperature and pressure range, since Palmer et al. disclose that the water, catalyst promoter, unreacted acetone and the unreacted phenol are removed from the crude polyphenol using distillation." Applicant respectfully disagrees.
Yoshitomi uses a bound catalyst promoter where part of the strong acid cation exchange catalyst is neutralized with an auxiliary catalyst like mercaptoalkylamine. Yoshitomi at col. 5, 11.
52-56. Accordingly, Yoshitomi does not disclose or teach the removal of an unbound catalyst promoter. Further, Yoshitomi does not disclose the composition of the residual stream or a desire to have a very low concentration of water in the residual stream. As such, Yoshitomi does not disclose or teach the residual stream composition or motivate one skilled in the art to apply the disclosed distillation conditions for the purpose of removing unbound catalyst promoter.
Further, none of the cited art discloses or teaches the composition of the residual stream or a motivation for the distillation step to remove high amounts of water, i.e., "a residual stream containing phenol, bisphenol A, the unbound catalyst promoter at less than 10 ppm by weight" or "a residual stream containing phenol, bisphenol A, the unbound catalyst promoter at less than 10 ppm by weight, the water at less than 50 ppm by weight and the unreacted acetone at less than 50 ppm by weight," the water at less than 100 ppm by weight and the unreacted acetone at less than 50 ppm by weight," emphasis added. Rather, Applicant submits that Yoshitomi teaches a high concentration of water is desired when treating a fluid with a basic anion exchange resin. Specifically, Yoshitomi states that the water concentration in the fluid treated to remove free acid should contain water at 0.01-1% by mass for the basic anion exchange resin to be effective. Yoshitomi at col. 4, 11. 26-29 and col. 8, 11. 44-57. While the treatment with the basic anion exchange resin in Yoshitomi is at a different location in the process, Yoshitomi clearly motivates one skilled in the art to have a concentration of water in the residual stream higher than the claimed water concentration. Therefore, Yoshitomi teaches away from the claimed composition of the residual stream.
Regarding new claim 16, Applicant submits that the as-filed application supports "the water at less than 50 ppm by weight." The application discloses water concentrations in the residual stream of (i) 1000 ppm or less at [0027], (i) 100 ppm or less of water at [0027], and (iii) 0 wt% at Examples 3 and 5. Accordingly, the as-filed application discloses a concentration of water in the residual stream may be in the range of 0 to 1000 ppm. Consistent with MPEP 2163.05, the citation of In re Wertheim, 541 F.2d 257, 191 USPQ 90 (CCPA 1976) supports that the disclosure of a range inherent discloses all of the endpoints along the range. Therefore, the residual stream including "the water at less than 50 ppm by weight" is supported by the as-filed application.”
This argument has been fully considered, but is not found to be persuasive. According to the new 103 rejections above, Palmer et al. discloses an unbound catalyst promoter (column 4, lines 62-67 and column 5, lines 1-3) and therefore the fact that Yoshitomi teaches a bound catalyst promoter is moot and would not discourage the skilled artisan from applying the teachings of Yoshitomi to the method of Palmer to arrive at the claimed invention. Furthermore, the argument that the cited prior art neither discloses nor teaches the composition of the residual stream or a motivation for the distillation step to remove high amounts of water, and that Yoshitomi clearly motivates one skilled in the art to have a concentration of water in the residual stream higher than the claimed water concentration in not persuasive in view of the new claim rejections detailed above. Of particular note, Yoshitomi teaches a process for producing bisphenol A wherein free acid is removed in the presence of 0.01 to 1% by mass of water in the free-acid removing step (claim 9). The lower end of this range as taught by Yoshitomi corresponds to 100 ppm of water and is therefore sufficiently close as to render obvious the instantly claimed range of less than 100 ppm by weight of water as recited in claims 1 and 14. MPEP § 2144.05(I) states that “a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close.” Finally, regarding the claim 16 limitation less than 50 ppm by weight of water, one of ordinary skill could reasonably arrive at this water content based on the teachings of Palmer and Yoshitomi through means of routine experimentation. MPEP § 2144.05(II) states that “[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation.” Therefore, the new claim rejections are maintained for the reasons of record and the reasons set forth above.
Conclusion
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/D.R./Examiner, Art Unit 1692
/Rayna Rodriguez/Primary Examiner, Art Unit 1628