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 .
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kaller (US Patent No. 10,106,486 B2).
Regarding claims 1 and 2, Kaller teaches a process for producing carboxylic acid esters and the use thereof as plasticizers in thermoplastic polymers (Abstract). The carboxylic acid esters are produced by reacting carboxylic acids with alcohols, which may be simple alcohols and a mixture thereof with alcohols comprising glycol subunits (c.f. col. 4, lines 13-18). The carboxylic acid is specifically indicated as including terephthalic acid (col. 5, lines 42-43); furthermore, the alcohols comprising glycol subunits are explicitly indicated as including unbranched C1-C12 and branched C3-C13 alkyl moieties (col. 4, lines 23-24). Finally, the alcohols comprising glycol subunits are indicated as having 1, 2, or 3 consecutive glycol units (c.f. col. 4, line 27, wherein variable n is indicated as having a value of 1, 2, or 3).
Regarding the newly added limitation requiring that the claimed “R1” is (C3-4) alkyl, Kaller teaches that the simple alcohols are explicitly indicated as including unbranched and branched C5-C13 alcohols (col. 4, lines 19-20), and thus the claimed (C3-4) alkyl (required by claim 1) and “butyl,” having an alkyl chain of C4 (required by claim 2) are lower than said range. However, Kaller specifically points out by reference that prior art documents have taught successful esterification reactions utilizing n-butanol (col. 3, lines 31-36), and teaches that because n-butanol has a boiling point of 117°C, processes involving n-butanol are preferably conducted between 115 and 150°C (i.e., at reflux, c.f. col. 3, lines 36-41), which overlaps with the temperature at which Kaller’s reaction is conducted (col. 4, line 35).
Moreover, Kaller teaches that the preferred catalyst for n-butanol reactions include sulfonic acids (col. 3, lines 39-41), which are also the catalyst specifically indicated within the inventive mixture (col. 4, lines 31-32). Finaly, Kaller does not teach away from the usage of C4 alcohols such as n-butanol; in fact, Kaller teaches the use of butyl-substituted versions of alcohols comprising glycol subunits, indicating that butyl groups are suitable within the molecular structure of the inventive plasticizers. It would have therefore been obvious to one having ordinary skill in the art at the time of filing to incorporate n-butanol as the simple alcohol within Kaller; in doing so, the esterification reaction product mixture described in the rejection of claim 1, above, would contain an ester product substituted with the simple alcohol on one side and the glycol-containing alcohol on the other side, wherein the simple alcohol (corresponding to the claimed “R1”) is an unbranched butyl group (which is a C4 group).
Alternatively, chemical structures may be made prima facie obvious due to close structural and chemical similarity (see MPEP 2144.IV.). In this case, Kaller teaches the use of C5 alkyl groups within the simple alcohol which are essentially methylated n-butanol (e.g., col. 6, lines 10-11 lists the incorporation of n-pentanol, 2-methylbutanol, and 3-methylbutanol). In each of these listed cases, the C5 alkyl groups differ from an n-butyl group by a single methyl group, which is merely the smallest possible increase in alkyl chain length above that of n-butanol. The addition of a methyl group in this way imparts no significant change to chemical reactivity or general function of the plasticizer composition. It would therefore have been obvious to one having ordinary skill in the art at the time of filing to include structures including n-butyl substituents within the inventive composition of Kaller, because of the disclosure of parallel compounds which are chemically similar thereto (i.e., n-pentanol, 2-methylbutanol, and 3-methylbutanol).
The reaction is conducted at elevated temperature (col. 4, line 35), in the presence of an acid catalyst for esterification (col. 4, lines 31-32). One having ordinary skill in the art would understand that this mixture of alcohols and carboxylic acids, under the aforementioned conditions (suitable for effecting an esterification reaction, c.f. col. 5, lines 42-43), would result in a mixed product containing terephthalate residues which have been (i) substituted with the simple alcohol on one side and the glycol-containing alcohol on the other side, (ii) substituted with the simple alcohol on both sides, and (iii) substituted with the glycol-containing alcohol on both sides. For the aforementioned reasons, the products (i) read on the claimed “compound of formula I.”
Regarding claim 3, Kaller teaches that 2-butoxyethanol is a particularly preferred glycol-containing alcohol within the inventive composition (col. 21, lines 64-65); 2-butoxyethanol corresponds to a glycol-containing alcohol substituent wherein the claimed “R2” is an unbranched butyl.
Regarding claim 4, Kaller is silent with regard to the claimed range. However, as described above, Kaller teaches a process of forming a plasticizer composition wherein terephthalic acid is reacted with a mixture of alcohols to produce a mixed plasticizer product. This process bears substantial similarities to the process contemplated within the instant application (c.f. instant Specification at pp. 16-17, wherein transesterification of dimethyl terephthalate is conducted in the presence of n-butanol and 2-butoxyethanol to produce a mixed ester product). Furthermore, the instant Specification contemplates that the feed ratio of n-butanol and 2-butoxyethanol directly governs the distribution of products (c.f. p. 17, Table 1).
Kaller is silent regarding the feed ratios of the simple alcohol and the glycol-containing alcohol. Nevertheless, the obviousness analysis may “take account of the inferences and creative steps that a person of ordinary skill in the art would employ.” KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 421 (2007). For example, the analysis may “include recourse to logic, judgment, and common sense available to the person of ordinary skill that do not necessarily require explication in any reference or expert opinion.” Perfect Web Techs., Inc. v. InfoUSA, Inc., 587 F.3d 1324, 1329 (Fed. Cir. 2009). The Patent Trial and Appeal Board has held that mixing equivalent components in a 1:1 ratio represented no more than application of the “logic, judgment, and common sense available to the person of ordinary skill” in the art. Ex parte Swanzy, Appeal 2017-004875 at 8-9.
In this case, Kaller discloses the simple alcohol and the glycol-containing alcohol as equally suitable alternatives to one another and therefore recognizes the equivalence of the two reagents in the context of the inventive plasticizer production method. It would have would have been prima facie obvious, using no more than ordinary creativity, logic, judgment, and common sense, to combine the simple alcohol and glycol-containing alcohol in equal amounts (i.e. in a 1:1 ratio) based on the fact that both are disclosed in parallel as being equally suitable for use in this capacity.
The instant Specification shows that a feed ratio of 1:1 between the aforementioned alcohols yields a distribution of products wherein the claimed compound of “formula I” is produced within the claimed range (p. 17, Table 1). Therefore, it is the office’s position that a feed ratio of 1:1 within the inventive process of Kaller, which is obvious as described above, would result in a product distribution whose compositional amounts of compounds reading of the claimed “formula I” would fall within the claimed range of “20 to 60 weight %,” establishing a prima facie case of obviousness.
Regarding claim 5, as described above, the inventive production method of Kaller would additionally result in a product which is substituted with the simple alcohol on both sides. These products read on the claimed “compound of formula II” because they overlap in scope when, within the claimed “formula II” R3 are each C-5-C6 alkyl groups.
Regarding claim 6, as described in the rejection of claim 4, above, it would have been obvious to one having ordinary skill in the art to include the simple and glycol-containing alcohols of Kaller in a feed ratio of 1:1 within the inventive process. The instant Specification shows that a feed ratio of 1:1 between the aforementioned alcohols yields a distribution of products wherein the claimed compound of “formula II” is produced within the claimed range (p. 17, Table 1). Therefore, it is the office’s position that a feed ratio of 1:1 would result in a product distribution whose compositional amounts of compounds reading of the claimed “formula II” would fall within the claimed range of “20 to 70 weight %,” establishing a prima facie case of obviousness.
Regarding claim 7, as described above, the inventive production method of Kaller would additionally result in a product which is substituted with the glycol-containing alcohol on both sides. These products read on the claimed “compound of formula III” because they overlap in scope when, within the claimed “formula III” R4 are each C1-C6 alkyl groups, and m are each integers of 1, 2, or 3.
Regarding claim 8, Kaller teaches that 2-butoxyethanol is a particularly preferred glycol-containing alcohol within the inventive composition (col. 21, lines 64-65); 2-butoxyethanol corresponds to a glycol-containing alcohol substituent wherein the claimed “R4” is an unbranched butyl.
Regarding claim 9, as described above, the use of n-butanol would have been obvious to one having ordinary skill in the art and 2-butoxyethanol is a particularly preferred glycol-containing alcohol within the inventive composition of Kaller (col. 21, lines 64-65); therefore, the resulting product mixture would contain all butyl groups in the claimed locations. Furthermore, the use of 2-butoxyethanol would yield m and n values of 1.
Regarding claim 10, as described in the rejection of claim 4, above, it would have been obvious to one having ordinary skill in the art to include the simple and glycol-containing alcohols of Kaller in a feed ratio of 1:1 within the inventive process. The instant Specification shows that a feed ratio of 1:1 between the aforementioned alcohols yields a distribution of products wherein the claimed compound of “formula III” is produced within the claimed range (p. 17, Table 1). Therefore, it is the office’s position that a feed ratio of 1:1 would result in a product distribution whose compositional amounts of compounds reading of the claimed “formula III” would fall within the claimed range of “2 to 30 weight %,” establishing a prima facie case of obviousness.
Regarding claims 11-12, as described above, the inventive production method of Kaller would result in a product which is substituted with the simple alcohol on one side and the glycol-containing alcohol on the other side. As described above, the use of n-butanol would have been obvious to one having ordinary skill in the art and 2-butoxyethanol is a particularly preferred glycol-containing alcohol within the inventive composition of Kaller (col. 21, lines 64-65); the product containing the simple alcohol on one side and the glycol-containing alcohol on the other side, produced from terephthalic acid, n-butanol, and 2-butoxyethanol, would be identical to the claimed compound of “formula IA” wherein “n” is 1.
Furthermore, as described in the rejection of claim 4, above, it would have been obvious to one having ordinary skill in the art to include the simple and glycol-containing alcohols of Kaller in a feed ratio of 1:1 within the inventive process. The instant Specification shows that a feed ratio of 1:1 between the aforementioned alcohols yields a distribution of products wherein the claimed compound of “formula I” is produced within the claimed range (p. 17, Table 1). “Formula IA” is a species structure corresponding to “formula I” when R1-2 are butyl and n is 1-2. Therefore, it is the office’s position that a feed ratio of 1:1 would result in a product distribution whose compositional amounts of compounds reading of the claimed “formula IA” would fall within the claimed range of “20 to 60 weight %,” establishing a prima facie case of obviousness.
Regarding claim 13, as described above, the inventive production method of Kaller would result in a product which is substituted with the simple alcohol both sides of the terephthalic acid residue. As described above, the use of n-butanol would have been obvious to one having ordinary skill in the art; the product containing the simple alcohol on both sides produced from terephthalic acid and n-butanol, in a mixture with 2-butoxyethanol, would be identical to the claimed compound of “formula IIA.”
Furthermore, as described in the rejection of claim 4, above, it would have been obvious to one having ordinary skill in the art to include the simple and glycol-containing alcohols of Kaller in a feed ratio of 1:1 within the inventive process. The instant Specification shows that a feed ratio of 1:1 between the aforementioned alcohols yields a distribution of products wherein the claimed compound of “formula II” is produced within the claimed range (p. 17, Table 1). “Formula IIA” is a species structure corresponding to “formula II” when R3 are both butyl. Therefore, it is the office’s position that a feed ratio of 1:1 would result in a product distribution whose compositional amounts of compounds reading of the claimed “formula IIA” would fall within the claimed range of “20 to 70 weight %,” establishing a prima facie case of obviousness.
Regarding claims 14-15, as described above, the inventive production method of Kaller would result in a product which is substituted with the glycol-containing alcohol both sides of the terephthalic acid residue. As described above, 2-butoxyethanol is a particularly preferred glycol-containing alcohol within the inventive composition of Kaller (col. 21, lines 64-65); the product containing the glycol-containing alcohol on both sides produced from terephthalic acid and 2-butoxyethanol, in a mixture with 2-butanol, would be identical to the claimed compound of “formula IIIA” wherein m (and also n) are each 1.
Furthermore, as described in the rejection of claim 4, above, it would have been obvious to one having ordinary skill in the art to include the simple and glycol-containing alcohols of Kaller in a feed ratio of 1:1 within the inventive process. The instant Specification shows that a feed ratio of 1:1 between the aforementioned alcohols yields a distribution of products wherein the claimed compound of “formula III” is produced within the claimed range (p. 17, Table 1). “Formula IIIA” is a species structure corresponding to “formula III” when R4 are both butyl and wherein m is 1. Therefore, it is the office’s position that a feed ratio of 1:1 would result in a product distribution whose compositional amounts of compounds reading of the claimed “formula IIIA” would fall within the claimed range of “2 to 30 weight %,” establishing a prima facie case of obviousness.
Regarding claims 16-20, Kaller teaches compounds “I” – “III,” as described above. Kaller further teaches the use thereof in thermoplastic polymers including, inter alia, PVC, vinyl acetate homo-and copolymers, and polyacrylates (col. 22, line 63 – col. 23, line 3).
Response to Arguments
Applicant’s arguments, see Applicant’s Remarks, filed June 19, 2026, with respect to 35 U.S.C. 112(b) have been fully considered and are persuasive. The 35 U.S.C. 112(b) rejection of claims 9 and 14 has been withdrawn.
Applicant's remaining arguments, with respect to 35 U.S.C. 103, have been fully considered but they are not persuasive.
Applicant argues that the amended range of “R1” groups now lies outside of the range taught by Kaller, as Kaller only teaches the use of alcohols with alkyl chains as small as C5. However, as described above, it would have been obvious to one having ordinary skill in the art to utilize a C4 alcohol, in view of Kaller’s disclosure of prior art documents having taught successful esterification reactions utilizing n-butanol (col. 3, lines 31-36). Also as described above, Kaller teaches that processes involving n-butanol are preferably conducted between 115 and 150°C (i.e., at reflux, c.f. col. 3, lines 36-41), which overlaps with the temperature at which Kaller’s reaction is conducted (col. 4, line 35).
Moreover, Kaller teaches that the preferred catalyst for n-butanol reactions include sulfonic acids (col. 3, lines 39-41), which are also the catalyst specifically indicated within the inventive mixture (col. 4, lines 31-32). Finaly, Kaller does not teach away from the usage of C4 alcohols such as n-butanol; in fact, Kaller teaches the use of butyl-substituted versions of alcohols comprising glycol subunits, indicating that butyl groups are suitable within the molecular structure of the inventive plasticizers.
As described above, assuming arguendo that Kaller does not disclose a teaching of butanol (and therefore a C4 alkyl chain), said chain differs from the explicit disclosure of Kaller merely by one methylene group (the smallest possible carbon chain difference). Therefore, the chemical structure is prima facie obvious due to close structural and chemical similarity (see MPEP 2144.IV.).
Applicant attempts to point to col. 3, lines 31-47 of Kaller to indicate that n-butanol is taught away from because the reaction temperature is too low, however, this passage specifically references a different document that successfully forms the n-butanol variant using a temperature from 115 to 150°C and a sulfonic acid catalyst. The applicant also points to col. 3, line 66 – col. 4, line 7 to assert that Kaller seeks to use elevated temperatures; however, as described above, Kaller specifically states that the suitable temperature range for the inventive process includes temperatures ranging from 125°C to 240°C and a sulfonic acid catalyst (col. 4, lines 30-35). These requirements are specifically aligned with what was disclosed in the prior art reference – the same acid catalyst, and a temperature range which overlaps that of Kaller’s design.
Applicant finally argues that the instant application appreciates particular benefits of the claimed composition; however, it is not necessary that the prior art appreciate the same characteristics as the applicant, as the discovery of a new property of a previously disclosed invention does not generally confer patentability (see MPEP 2112.I.).
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
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/JOSHUA CALEB BLEDSOE/Examiner, Art Unit 1762
/MARK EASHOO/Supervisory Patent Examiner, Art Unit 1767
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