DETAILED ACTION
Notice of Pre-AIA or AIA Status
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
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and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114.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 March 2, 2026 has been entered.
Claims 16-32 are pending as amended on March 2, 2026. Support for amended claim 16 and new claims 31-32 is found in original claim 16. Claims 28-30 stand withdrawn from consideration.
Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in the action can be found in a prior Office action.
Claim Objections
Claims 17 and 26 are objected to because of the following informalities:
In claim 17, “Ia” and “Ib” should read “1a” and “1b” to be consistent with the Arabic numerals used in claim 16.
In claim 26, line 8, “bisphenol M, the bisphenols (V) to (VII)” should read “bisphenol M, and the bisphenols (V) to (VII).”
Appropriate correction is required.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claims 16-27 and 31 are rejected under 35 U.S.C. 103 as being obvious over Meyer (WO 2020035519 A1, published 2/20/2020, US 20220119334 A1 is used as an English translation) in view of Sakashita (US 5,880,248).
Regarding claims 16-20, 22-27, and 31, Meyer teaches a process for preparing a polyester carbonate (Meyer, Abstract). Meyer teaches reacting a mixture comprising at least one cycloaliphatic dicarboxylic acid and at least one aliphatic and/or aromatic carbonate, in the presence of at least a first catalyst that is basic, to form a cycloaliphatic diester of formula (Ia) or (Ib):
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in which each A is independently an aliphatic or aromatic radical and n is a number between 0 and 3 (Meyer, [0016-0021]). This reads on instant step (i) where D in formula (1) is formula (1a) or (1b) in which B is a CH2 group (claim 17), m is 0, n is a number between 0 and 3, and R1 is a bond.
As the cycloaliphatic dicarboxylic acid, Meyer prefers cyclohexane-1,4-dicarboxylic acid (Meyer, [0042]) (claim 18). As the aromatic carbonate, Meyer suggests an aromatic carbonate of reading on formula (III) where R, R’, and R’’ may each independently be identical or different and represent hydrogen, optionally branched C1-C34 alkyl, C7-C34 alkylaryl or C6-C34 aryl and R may also denote -COO-R’’’, where R’’’ represents optionally branched C1-C34 alkyl, C7-C34 alkylaryl, or C6-C34 aryl (Meyer, [0043-0044]) (claim 19). As the first catalyst, Meyer teaches basic catalysts such as cesium carbonate (Cs2CO3), sodium phenoxide (sodium phenolate), and 4-dimethylamine pyridine (Meyer, [0049-0050]) (claim 20).
Meyer further teaches separating the cycloaliphatic diester from the mixture of step (i) by means of distillation (Meyer, [0022]), reading on instant step (ii).
Meyer then reacts the cycloaliphatic diester of formula (Ia) or (Ib), at least one dihydroxy compound, and at least one diaryl carbonate in a melt transesterification process (Meyer, [0064]). The hydroxy compounds listed in [0068] are identical to those in instant claim 26. Meyer also teaches hydroxy compounds selected from isomannide, isoidide, and isosorbide, and mixtures thereof (Meyer, [0071]) (claim 27). This step corresponds to instant step (iii).
As the catalyst for step (iii), Meyer teaches condensation catalysts known in the art (Meyer, [0065]). As examples, Meyer points to alkali metal compounds, alkaline earth metal compounds, quaternary ammonium compounds, quaternary phosphonium compounds, and any desired combination thereof (Meyer, [0065]). Meyer exemplifies a mixture of 50 ppm cesium carbonate and 50 ppm of sodium hydroxide (NaOH) (Meyer, [0129]). NaOH reads on a basic alkali metal salt. A content of 50 ppm NaOH corresponds to about 0.0029 wt% of sodium metal cations based on all components used in process step (iii) (50 ppm = 0.005 wt% and NaOH is 57.5% Na (23/40=0.575)).
Meyer teaches the third catalyst (NaOH) in the claimed amount and teaches mixtures of catalysts, but does not teach a tertiary nitrogen base as the second catalyst.
However, Sakashita teaches polycarbonates prepared by melt polycondensation (Sakashita, col. 2, lines 18-23) and utilizes catalyst mixtures. Like Meyer, Sakashita teaches dihydroxy compounds including BPA (Sakashita, col. 4, lines 27-29) and aromatic carbonates such as diphenyl carbonate (Sakashita, col. 6, lines 23-25). Sakashita teaches that using a combination of an alkali compound and a nitrogen-containing compound as a catalyst makes it possible to carry out the polycondensation with a high level of activity and produce high-molecular weight copolycarbonates which show outstanding thermal resistance, water resistance, color-matching properties, and transparency (Sakashita, col. 8, lines 46-52). Examples of the alkali compound of Sakashita include sodium hydroxide (Sakashita, col. 7, lines 4-5). Sakashita’s examples of nitrogen-containing basic compounds include tertiary amines and pyridines such as 4-dimethylaminopyridine (also reading on tertiary amines) (Sakashita, col. 7, line 54 to col. 8, line 3). Sakashita teaches using 1x10-8 to 1x10-3 moles of alkali compound (Sakashita, col. 7, lines 33-36) and 1x10-5 to 1x10-2 moles of nitrogen-containing basic compound (Sakashita, col. 5, lines 16-19) with respect to 1 mole of diol.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have substituted the condensation catalyst of Meyer for the mixture of an alkali compound and nitrogen-containing basic compound taught by Sakashita in order to carry out the polycondensation with a high level of activity and to produce high-molecular weight copolycarbonates with outstanding thermal resistance, water resistance, color-matching properties, and transparency. It would have further been obvious to select any combination of alkali compound and nitrogen-containing basic compound from those taught by Sakashita in the amounts taught by Sakashita, including a mixture of 1x10-8 to 1x10-3 moles of sodium hydroxide (claim 24-25) and 1x10-5 to 1x10-2 moles of 4-dimethylaminopyridine (DMAP) (claim 23) based on 1 mole of diol. One would have had a reasonable expectation of successfully producing the copolyester carbonate of Meyer because Meyer teaches that condensation catalysts known to those skilled in the art can be used (Meyer, [0065]).
The second and third catalyst contents of modified Meyer are broader than the claimed ranges.
However, the ranges taught by modified Meyer overlap with the claimed ranges. To estimate the catalyst contents in weight percent, the monomer ratios of Meyer’s Example A are taken as a representative example of a suitable monomer ratio. Example A teaches polymerizing 0.0246 mol (8 g) of cycloaliphatic diester, 0.0616 mol diol, and 0.0387 mol (8.3 g) of diphenyl carbonate (Meyer, [0129]). Based on 0.0616 moles of diol, one would use 0.0616x10-8 to 0.0616x10-3 moles of sodium cations and 0.0616x10-5 to 0.0616x10-2 moles of DMAP or 1.4x10-8 to 1.4x10-3 g of sodium cations and 7.5x10-5 to 7.5x10-2 g of DMAP. In the case where the diol is bisphenol A, the carbonate is diphenyl carbonate, and the cycloaliphatic diester is diphenyl cyclohexane-1,4-dicarboxylate, the total mass of the reaction mixture would be about 30.34 (8+8.3+0.0616*228). The sodium cation content is therefore about 0.000000047-0.0047 wt% and the 4-methylaminopyridine content is about 0.00024-0.24 wt%. It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have used any sodium cation content in the range of about 0.000000047-0.0047 wt% and any 4-methylaminopyridine content in the range of about 0.00024-0.24 wt% because modified Meyer teaches these ranges. A sodium cation range of about 0.000000047-0.0047 wt% overlaps with the claimed alkali metal cation contents of 0.0010% to 0.0030% by weight (claim 16) and 0.00108% to 0.00252% by weight (claim 31). A second catalyst (DMAP) range of about 0.00024-0.24 wt% overlaps with the claimed range of 0.005% to 0.02% by weight (claim 22). It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
Regarding claim 21, modified Meyer teaches the process of claim 16. Meyer teaches using the catalysts in an amount of 10-2 to 10-8 mol based on 1 mole of cycloaliphatic dicarboxylic acid (Meyer, [0051]). Meyer further exemplifies using 0.024 wt% of the first catalyst in example 1 (Meyer, [0095]). Example 1 uses 3.44 g of diacid, 8.99 g of diphenyl carbonate, and 0.0031 g of sodium phenolate trihydrate as the catalyst, corresponding to a first catalysts content of about 0.024 wt% in step (i).
Claims 16-19, 21-26, and 31-32 are rejected under 35 U.S.C. 103 as being unpatentable over Whitney (WO 02/10111 A1, Cite No. 3 on 6/22/2022 IDS) in view of Sakashita (US 5,880,248) and evidenced by Quattrosoldi (Fully biobased, elastomeric and compostable random copolyesters of poly(butylene succinate) containing Pripol 1009 moieties: Structure-property relationship, Polymer Degradation and Stability, 2020, 178, 109189).
Regarding claims 16-19, 22-26, and 31, Whitney teaches a process for preparing a polyester carbonate (Whitney, page 10, line 6). In the process of Whitney, diaryl esters are prepared by the transesterification reaction of a diaryl carbonate and an aliphatic diacid (Whitney, page 4, lines 26-27). The reaction may be conducted in the presence of a base catalyst (Whitney, page 7, lines 14-15). In example 6, Whitney exemplifies preparing a diaryl ester from a C36 dimer acid with the tradename of Pripol 1009 and diphenyl carbonate (Whitney, page 23, lines 1-9). It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have selected Pripol 1009 as the aliphatic diacid and diphenyl carbonate as the diaryl carbonate because Whitney teaches this combination. Diphenyl carbonate reads on an aromatic carbonate of formula (III) wherein R, R’, and R’’ are each hydrogen (claim 19). Pripol 1009 reads on a hydrogenated dimer fatty acid (claim 18). As evidenced by Quattrosoldi, Pripol 1009 has the structure shown below (Quattrosoldi, page 2):
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The diaryl ester resulting from Pripol 1009 and diphenyl carbonate reads on formula (1) where A is an aromatic radical (phenyl) and D is formula (1a) where R1 is an alkylene group having 6 carbon atoms, B is CH2 (claim 17), n is 1, m is 2, and R2 is an alkyl group having 7-9 carbon atoms. This method reads on a method comprising the step of (i) reacting a mixture comprising a cycloaliphatic dicarboxylic acid (Pripol 1009) and an aromatic carbonate (diphenyl carbonate), in the presence of a first catalyst that is basic, to form an aliphatic diester of formula (1).
Whitney further teaches (ii) separating the aliphatic diester of formula (1) from the mixture from process step (i) (Whitney, page 9, lines 19-21).
Whitney then teaches (iii) reacting the separated aliphatic diester of formula (1), at least one dihydroxy compound, and at least one diaryl carbonate in a melt transesterification process (Whitney, page 10, lines 13-17 and page 16, lines 4-5) in the presence of a mixture of tetramethylammonium hydroxide and sodium hydroxide (NaOH) as the catalyst (Whitney, page 18, lines 15-16; Examples 8 and 9 use mixtures of tetramethylammonium hydroxide and NaOH, page 23-24). A mixture of tetramethylammonium hydroxide and NaOH corresponds to a second and third catalyst wherein the third catalyst is a basic alkali metal salt (NaOH). Whitney’s dihydroxy compounds include BPA (Whitney, page 12, line 6) (claim 26).
Whitney does not teach wherein the second catalyst is a tertiary nitrogen base.
However, prior to the effective filing date of the claimed invention, mixtures of basic alkali metal salts and tertiary nitrogen bases were known as alternatives to mixtures of basic alkali metal salts and tetramethylammonium hydroxide in the synthesis of polycarbonates, as evidenced by Sakashita.
Sakashita teaches polycarbonates prepared by melt polycondensation (Sakashita, col. 2, lines 18-23). Sakashita teaches that using a combination of an alkali compound and a nitrogen-containing compound as a catalyst makes it possible to carry out the polycondensation with a high level of activity and to produce high-molecular weight copolycarbonates which show outstanding thermal resistance, water resistance, color-matching properties, and transparency (Sakashita, col. 8, lines 46-52). Examples of the alkali compound of Sakashita include NaOH (Sakahita, col. 7, lines 4-5). Tetramethylammonium hydroxide, tertiary amines, and pyridines such as 4-dimethylaminopyridine (reading on tertiary amines) are listed as examples of the nitrogen-containing basic compound (Sakashita, col. 7, line 54 to col. 8, line 3). Sakashita teaches using 1x10-8 to 1x10-3 moles of alkali compound (Sakashita, col. 7, lines 33-36) and 1x10-5 to 1x10-2 moles of nitrogen-containing basic compound (Sakashita, col. 5, lines 16-19) with respect to 1 mole of diol. Given the disclosure of Sakashita, it is evident that catalyst mixtures of tertiary amines and NaOH were known as alternatives to mixtures of tetramethylammonium hydroxide and NaOH. Therefore, one of ordinary skill in the art would have recognized that the tetramethylammonium hydroxide-containing catalyst mixture of Whitney could be substituted with the tertiary amine-containing catalyst mixture of Sakashita.
Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR International Co. v. Teleflex Inc., 550 U.S. 398 (2007). MPEP § 2143, rationale (B). It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have substituted the tetramethylammonium hydroxide and NaOH catalyst mixture of Whitney with the tertiary amine and NaOH catalyst mixture of Sakashita. It would have further been obvious to select a combination of NaOH and any nitrogen-containing basic compound from those taught by Sakashita in the amounts taught by Sakashita, including a mixture of 1x10-8 to 1x10-3 moles of NaOH (claim 24-25) and 1x10-5 to 1x10-2 moles of 4-dimethylaminopyridine (DMAP) (claim 23) based on 1 mole of diol. One would have had a reasonable expectation of successfully catalyzing the polymerization of Whitney because both Whitney and Sakashita utilize BPA as a dihydroxy compound (see Sakashita Table 1; Whitney, page 12, line 6) and diphenyl carbonate as a diaryl carbonate (Sakashita, col. 6, lines 23-25; Whitney, page 16, line 12). Furthermore, Sakashita teaches that using an alkali compound with a nitrogen-containing compound as a catalyst makes it possible to carry out polycondensation with a high level of activity.
The second and third catalyst contents of modified Whitney are broader than the claimed ranges.
However, the ranges taught by modified Whitney overlap with the claimed ranges. The proportion of each catalyst can be estimated using the monomer composition of Whitney’s example 8 as representative of an appropriate quantity of each component in the polymerization mixture. Example 8 uses 256.81 g (1.099 moles) of diphenyl carbonate as the diaryl carbonate, 234.268 g (1.027 moles) of bisphenol-A as the dihydroxy compound, and 0.063 moles of the diphenyl ester (Whitney, page 23, lines 26-29). A content of 1.027 moles of the dihydroxy compound corresponds to 1.027x10-8 moles to 1.027x10-3 moles of alkali metal compound. Using NaOH as the alkali metal compound, this is equivalent to 2.4x10-7 g to 0.024 g of Na+ (Na MW=23 g/mol). The total mass of a mixture using the molar ratios of Whitney’s example 8 and a diphenyl ester derived from diphenyl carbonate and Pripol 1009 (MW is about (12.6 g/0.022 mol) + 2*77 g/mol = 727 g/mol) is about 537 g (256.81+234.268+0.063*(727)). The Na+ content is therefore about 0.000000044% to about 0.0044% by weight based on all components. A content of 1.027 moles of the dihydroxy compound corresponds to about 1.027x10-5 moles to 1.027x10-2 moles of tertiary amine. Using DMAP (MW=122 g/mol) as the tertiary amine, this is equivalent to 0.0013 g to 1.3 g or about 0.0002% to about 0.24% by weight based on all components.
It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have selected any Na+ content in the range of about 0.000000044% to about 0.0044% and any DMAP content in the range of about 0.0002% to about 0.24% because modified Whitney teaches these ranges. A Na+ range of about 0.000000044% to about 0.0044% overlaps with the claimed alkali metal cation range of 0.0010% to 0.0030% by weight (claim 16) and 0.00108% to 0.00252% by weight (claim 31). A DMAP range of about 0.0002% to about 0.24% overlaps with the claimed second catalyst range of 0.005% to 0.02% by weight (claim 22). It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
Regarding claim 21, modified Whitney teaches the process of claim 16.
Example 6 (Whitney, page 23, lines 1-9) demonstrates step (i), but does not anticipate a first catalyst content within the claimed range of 0.005% to 0.02% in step (i).
However, Whitney teaches that the first catalyst is used in an amount of 0.001 to 0.02 molar equivalents, based on the diacid (Whitney, page 8, lines 22-23). For the quantity of Pripol 1009 used in example 6 (0.022 moles), this corresponds to 0.000022-0.00044 moles of catalyst. For the tetramethylammonium hydroxide catalyst used in example 6 (MW=91 g/mol), this corresponds to 0.002-0.040 g of first catalyst. The overall mixture is approximately 27 g (12.6+14.4), so the content of first catalyst is about 0.007% to 0.148% based on the weight of all components used in process step (i).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have used any amount in the range of from 0.007% to 0.148% because modified Whitney teaches this range. A range of 0.007% to 0.148% overlaps with the claimed range of 0.005% to 0.2%. It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I
Regarding claim 32, modified Whitney teaches the process of claim 16. Whitney teaches that the dicarboxylic acid is selected from the group consisting of adipic acid, sebacic acid, dodecanedioic acid, octadecanedioic acid, C-19 dimer diacid, C-36 dimer diacid, terephthalic acid, and isophthalic acid and combinations thereof (Whitney, page 27, lines 3-6). It would have been obvious to one of ordinary skill prior to the effective filing date to have used any two of these diacids, including a mixture of dodecanedioic acid and a C-36 dimer diacid (Pripol 1009) because Whitney teaches combinations of these dicarboxylic acids. Including dodecanedioic acid in the dicarboxylic acid component reads on the mixture further comprising a linear aliphatic dicarboxylic acid.
Claim 20 is rejected under 35 U.S.C. 103 as being unpatentable over Whitney (WO 02/10111 A1, Cite No. 3 on 6/22/2022 IDS) in view of Sakashita (US 5,880,248) and evidenced by Quattrosoldi (Fully biobased, elastomeric and compostable random copolyesters of poly(butylene succinate) containing Pripol 1009 moieties: Structure-property relationship, Polymer Degradation and Stability, 2020, 178, 109189) as applied to claim 16 above, and further in view of Grieshaber (US 2017/0158853 A1).
Modified Whitney teaches the process of claim 16. Whitney teaches that the catalyst in process step (i) can be an alkali hydroxide (Whitney, page 8, lines 15-21).
Whitney does not teach that the catalyst is sodium phenoxide.
However, prior to the effective filing date of the claimed invention, sodium phenoxide was known as an alternative transesterification catalyst to alkali hydroxides such as NaOH, as evidenced by Grieshaber. Grieshaber teaches polycarbonates prepared by a melt transesterification process (Grieshaber, [0098]). Grieshaber’s transesterification catalysts include NaOH and sodium phenoxide (Grieshaber, [0100]). Given the disclosure of Grieshaber, it is evident that sodium phenoxide was known as an alternative transesterification catalyst to alkali hydroxides. Therefore, one of ordinary skill in the art would have recognized that the alkali hydroxide catalyst of Whitney could be substituted with the sodium phenoxide catalyst of Grieshaber.
Case law has established that it is prima facie obvious to substitute one known element for another to obtain predictable results. KSR International Co. v. Teleflex Inc., 550 U.S. 398 (2007). MPEP § 2143, rationale (B). It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have substituted the alkali hydroxide catalyst of Whitney with the sodium phenoxide catalyst of Grieshaber in process step (i). One would have had a reasonable expectation of successfully producing a diaryl ester because sodium phenoxide is an alkali transesterification catalyst and the method of Grieshaber teaches aliphatic diacid monomers (Grieshaber, [0098] and [0016]).
Claim 27 is rejected under 35 U.S.C. 103 as being unpatentable over Whitney (WO 02/10111 A1, Cite No. 3 on 6/22/2022 IDS) in view of Sakashita (US 5,880,248) and evidenced by Quattrosoldi (Fully biobased, elastomeric and compostable random copolyesters of poly(butylene succinate) containing Pripol 1009 moieties: Structure-property relationship, Polymer Degradation and Stability, 2020, 178, 109189) as applied to claim 16 above, and further in view of Oh (WO 2019/147051, Cite No. 4 on 6/22/2022 IDS, US 2020/0362105 A1 is used as an English translation).
Modified Whitney teaches the process of claim 16 where the dihydroxy compound is bisphenol A (Whitney, page 12, line 6).
Whitney does not teach wherein at least one dihydroxy compound in process step (iii) is selected from the group consisting of isomannide, isoidide, and isosorbide.
However, Oh teaches bio-based polycarbonate esters prepared by melt-polycondensation of monomers including 1,4:3,6-dianhydrohexitols such as isomannide, isoidide, and isosorbide (Oh, [0002] and [0023]). Oh teaches that where 1,4:3,6-dianhydrohexitol is used as a monomer for preparing a polycarbonate, the polycarbonate thus prepared has high heat resistance and transparency as well as excellent surface hardness, UV stability, flame retardance, and chemical resistance, along with the advantages of a bioplastic (Oh, [0002]) and that the polycarbonate ester is environmentally friendly since it is free from bisphenol (Oh, [0014]). Oh further teaches that as compared with the polycondensation process of a bisphenol A polycarbonate which requires high reaction temperature due to high melt viscosity, the melt-polycondensation process of bio-based polycarbonate esters derived from 1,4:3,6-dianhydrohexitol can be carried out at a low reaction temperature, preventing discoloration and deterioration of the physical properties of the product (Oh, [0061]).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have substituted the bisphenol A of Whitney for the isomannide, isoidide, or isosorbide of Oh in order to make the polyester carbonate more environmentally friendly, reduce the reaction temperature, and prevent discoloration and deterioration of the polyester carbonate.
Response to Arguments
Applicant's arguments filed March 2, 2026 have been fully considered.
Applicant argues (page 8) that Whitney does not demonstrate that the process can be executed with cycloaliphatic diacids. This argument is not persuasive because Whitney teaches that the aliphatic diacid can be a branched or unbranched cycloalkyl (Whitney, page 7, lines 1-8) and exemplifies Pripol 1009 in Example 6 (Whitney, page 23, line 4). While Whitney does not exemplify the full process of making a polyester carbonate using a cycloaliphatic diacid, this does not negate a finding of obviousness under 35 USC 103 since a preferred embodiment such as an example is not controlling. Rather, all disclosures “including unpreferred embodiments” must be considered. In re Lamberti 192 USPQ 278, 280 (CCPA 1976) citing In re Mills 176 USPQ 196 (CCPA 1972). Therefore, it would have been obvious to one of ordinary skill in the art to utilize a cycloaliphatic diacid given that Whitney teaches one.
Applicant argues (page 8) that cycloaliphatic dicarboxylic acids are less thermally stable than linear dicarboxylic acids and thus, the production of cycloaliphatic polyester carbonates poses problems for those or ordinary skill in the art. MPEP 716.01(c) II states that arguments presented by the applicant cannot take the place of evidence in the record. In re Schulze, 346 F.2d 600, 602, 145 USPQ 716, 718 (CCPA 1965). As evidence, Applicant points to [0010] and [0011] of the published application. The application argue that Whitney does not demonstrate the process with cycloaliphatic diacids and states that cycloaliphatic diacids are usually less thermally stable. This is not sufficient evidence that cycloaliphatic diacids are less stable and that one would not be able to rely on the teachings of Whitney when making cycloaliphatic polyester carbonates. As discussed above, Whitney teaches that the aliphatic diacid can be a branched or unbranched cycloalkyl (Whitney, page 7, lines 1-8).
Applicant argues (page 9) that the first basic catalyst is necessary for the reaction between the aliphatic and/or aromatic carbonate and the cycloaliphatic dicarboxylic acid to take place, but that Whitney teaches that the products obtained in the presence of a base catalyst will have more impurities than products obtained in the absence of a base catalyst. While Whitney acknowledges a trade-off between reaction rate and product purity (Whitney, page 8, lines 14-25), Whitney teaches utilizing a base catalyst, as claimed. MPEP 2123 II states, “[t]he prior art’s mere disclosure of more than one alternative does not constitute a teaching away from any of these alternatives because such disclosure does not criticize, discredit, or otherwise discourage the solution claimed….” In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004). It would therefore have been obvious to one of ordinary skill to use a base catalyst in order to increase the reaction rate because Whitney teaches using a base catalyst to increase the reaction rate. In addition, Applicant has not demonstrated that the claimed basic catalyst does not lead to the impurities noted by Whitney.
Applicant argues (page 9-12) that the claimed proportion of alkali metal cations in process step (iii) of 0.0010% to 0.0030% by weight based on all components used in process step (iii) is critical for obtaining a cycloaliphatic polyester carbonate having adequate polymer growth without severe degradation. Applicants can rebut a prima facie case of obviousness by showing the criticality of the range. See MPEP 2144.05 III. As evidence, Applicant points to the examples in Table 1. These examples demonstrate process step (iii) for a mixture of 59.96 g isosorbide, 51.73 g of diphenyl carbonate, and 57.05 g of diphenyl cyclohexane-1,4-dicarboxylate. Experiments 1b-7b use a mixture of 53.3 ppm of N,N-dimethylaminopyridine (DMAP) and 3.6-36.0 ppm of sodium phenoxide trihydrate as the catalyst. Applicant designates Experiments 2b (3.6 ppm Na+) and 3b (7.2 ppm Na+) as non-inventive and observes that the relative viscosity is 1.16 and the produce is brittle. In contrast, Experiments 1b and 4b-6b encompass 10.8-25.2 ppm Na+, viscosities of 1.20-1.22, and are considered to be not brittle and inventive. Example 7b has more Na+ ions (36 ppm), a higher viscosity, and is observed to be brown and opaque. Experiments 8b-10b shows that 133.3 ppm of Na+, 2.0 ppm of Cs2CO3, or 133 ppm of Cs2CO3 alone are not sufficient to catalyze polymerization. Experiments 11b-13b use 667 ppm of either Cs2CO3, DMAP, or sodium phenoxide trihydrate (90.1 ppm Na+) lead to brittle products. The Applicant has not specified a quantitative measure of what is considered brittle or not brittle or of what is considered light-colored and transparent.
MPEP 716.02(b) states that appellants have the burden of explaining the data in any declaration they proffer as evidence of non-obviousness. Ex parte Ishizaka, 24 USPQ2d 1621, 1624 (Bd. Pat. App. & Inter. 1992). Applicant has not sufficiently explained the data provided in Table 1 because Applicant has not compared the data to the closest prior art or described how the data demonstrate an unexpected result. Applicant has not explained why one would not expect higher viscosity when the amount of catalyst is increased (Experiment 3b vs 4b and 6b vs 7b). Similarly, Applicant has not explained why the occurrence of a darker color with more alkali metal cations in the catalyst is unexpected. Furthermore, Applicant has not provided sufficient evidence to demonstrate the criticality of the upper limits of the claimed range of alkali metal cations because the claimed upper limit of alkali metal cations (0.0030 wt%) extends above the exemplified range of 25.2 ppm (0.0025 wt%).
In addition, evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support. See MPEP 716.02(d). Examples 1b and 4b-7b are not commensurate in scope with claim 16 at least because they utilize only isosorbide as the dihydroxy compound, diphenyl carbonate as the diaryl carbonate, and diphenyl cyclohexane-1,4-dicarboxylate as the cycloaliphatic diester of formula 1, DMAP as the second catalyst, and sodium phenoxide trihydrate as the third catalyst. Claim 16 encompasses numerous additional monomers and catalysts. In addition, claim 16 does not limit the relative amount of each monomer or first catalysts and does not limit reaction conditions such as the polymerization temperature, pressure, and time. If Applicant wishes to overcome the present rejection by showing unexpected results, Applicant must provide sufficient evidence to show that unexpected results would be obtained for all species and the full breath of ranges encompassed by the claims.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AUDRA DESTEFANO whose telephone number is (703)756-1404. The examiner can normally be reached Monday-Friday 9-5.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at (571)272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
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