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 .
Status of the Application
Claims 1-10 are pending and under current examination.
Amendment necessitated new claim rejection as set forth below.
Claim Rejections - 35 USC § 102
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 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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-2 and 9 are rejected under 35 U.S.C. 102(a)(1) and 102 (a)(2) as being anticipated by Kim (US 2014/0319097 A1).
Kim discloses a method of making a resist underlayer film using a pure (thus reads on 99.5% purity, 99.8%) 1,6-naphtalene dithiol with no impurity of polymeric 1,6-naphtalene dithiol. Since the cited prior art teaches same compound with no impurity, the Gardner color scale value of 1,6-naphtalene dithiol of the cited prior art is expected to be the same.
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Since the cited prior art reads on all the limitations of the instant claims 1-2 and 9, these claims are anticipated.
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 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 of this title, 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 text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
The factual inquiries set forth in Graham v. John Deere Co., 383 U.S. 1, 148 USPQ 459 (1966), that are applied 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.
This application currently names joint inventors. In considering patentability of the claims the examiner presumes that the subject matter of the various claims was commonly owned as of the effective filing date of the claimed invention(s) absent any evidence to the contrary. Applicant is advised of the obligation under 37 CFR 1.56 to point out the inventor and effective filing dates of each claim that was not commonly owned as of the effective filing date of the later invention in order for the examiner to consider the applicability of 35 U.S.C. 102(b)(2)(C) for any potential 35 U.S.C. 102(a)(2) prior art against the later invention.
Claims 1-10 are rejected under 35 U.S.C. 103 as being unpatentable over Rule (US 5338886) and Kim (US 2014/0319097 A1) in combination.
Determining the scope and contents of the prior art
Kim discloses a method of making a resist underlayer film using a pure (thus reads on 99.5% purity, 99.8%) 1,6-naphtalene dithiol with no impurity of polymeric 1,6-naphtalene dithiol. Since the cited prior art teaches same compound with no impurity, the Gardner color scale value of 1,6-naphtalene dithiol of the cited prior art is expected to be the same.
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Rule teaches a method of making naphthalene dithiol (encompass 1,6-naphthalene dithiol of the instant claims) followed by purification of the crude product using precipitation, vacuum drying and crystallization with no impurities of polymeric dithiol (entire patent, especially example 2).
Ascertaining the differences between the prior art and the claims at issue
Kim discloses a method of making a resist underlayer film using a pure (thus reads on 99.5% purity, 99.8%) 1,6-naphtalene dithiol with no impurity of polymeric 1,6-naphtalene dithiol. Since the cited prior art teaches same compound with no impurity, the Gardner color scale value of 1,6-naphtalene dithiol of the cited prior art is expected to be the same. However, the cited prior art fails to teach process of purification of 1,6-naphtalene dithiol.
Rule teaches a method of making naphthalene dithiol (encompass 1,6-naphthalene dithiol of the instant claims) followed by purification of the crude product using precipitation, vacuum drying, solvent extraction and crystallization to pure product with no impurities of polymeric dithiol but fails to teach purification using distillation.
Resolving the level of ordinary skill in the pertinent art
With regards to the above difference of purification and purification using distillation- Kim discloses a method of making a resist underlayer film using a pure (thus reads on 99.5% purity, 99.8%) 1,6-naphtalene dithiol with no impurity of polymeric 1,6-naphtalene dithiol. Rule teaches a method of purification of crude product of naphthalene dithiol using precipitation, vacuum drying, solvent extraction and crystallization to pure product. Thus, based on the teaching of Kim and Rule, it would have been prima facie obvious to a person of ordinary skill in the art to purify 1,6-naphtalene dithiol using procedure, such as using precipitation, vacuum drying, solvent extraction and crystallization to pure product as taught by Rule or to purify it by any common methods known in the art, such as distillation, HPLC etc., for its use in making resist underlayer film using pure form as taught by Kim. Given routine use of purification procedures in chemistry, such as crystallization, distillation, and column purification, it would have been prima facie obvious to a person of ordinary skill in the art with a reasonable expectation of success to use any of these processes to accomplish purification of crude product under conditions, such as heating and cooling for crystallization process, vacuum or under reduced pressure distilling and collecting at the boiling point of desired compound, or using a purification column, such as HPLC for purification.
Factors to be considered in determining whether a purified form of an old product is obvious over the prior art include whether the claimed chemical compound or composition has the same utility as closely related materials in the prior art, and whether the prior art suggests the particular form or structure of the claimed material or suitable methods of obtaining that form or structure. In re Cofer, 354 F.2d 664, 148 USPQ 268 (CCPA 1966) (Claims to the free-flowing crystalline form of a compound were held nonobvious over references disclosing the viscous liquid form of the same compound because the prior art of record did not suggest the claimed compound in crystalline form or how to obtain such crystals.). However, in the case of product-by-process claims, if a first prior art process is improved to enhance the purity of the product produced by the process, and if the purified product has no structural or functional difference from the products produced by other prior art processes, then the improvement in the first process that improves the purity of the product does not give rise to patentability. See Purdue Pharma v. Epic Pharma, 811 F.3d 1345, 117 USPQ2d 1733 (Fed. Cir. 2016).
Based on the above established facts, it appears that the teachings of above cited prior art read applicants’ compound and process.
Therefore, all the claimed elements were known in the prior art and one skilled person in the art could have combined the elements as claimed by known methods with no change in their respective functions, and the combination would have yielded predictable results to one of ordinary skill in the art at the time of the invention.
Considering objective evidence present in the application indicating obviousness or nonobviousness
To establish a prima facie case of obviousness, three basic criteria must be met: (1) the prior art reference must teach or suggest all the claim limitations; (2) there must be some suggestion or motivation, either in the references themselves or in the knowledge generally available to one of ordinary skill in the art, to modify the reference or to combine reference teachings; and (3) there must be a reasonable expectation of success; and (MPEP § 2143).
In this case, Kim discloses a method of making a resist underlayer film using a pure (thus reads on 99.5% purity, 99.8%) 1,6-naphtalene dithiol with no impurity of polymeric 1,6-naphtalene dithiol and Rule teaches a method of purification of crude product of naphthalene dithiol using precipitation, vacuum drying, solvent extraction and crystallization to pure product.
In KSR International Vo. V. Teleflex Inc., 82 USPQ2d (U.S. 2007), the Supreme Court particularly emphasized “the need for caution in granting a patent based on a combination of elements found in the prior art,” (Id. At 1395) and discussed circumstances in which a patent might be determined to be obvious. Importantly, the Supreme Court reaffirmed principles based on its precedent that “[t]he combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results.” (Id. At 1395). See MPEP 2143 - Examples of Basic Requirements of a Prima Facie Case of Obviousness [R-9].
In this case at least prong (E) “Obvious to try” – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success would apply.
The rationale to support a conclusion that the claim would have been obvious is that “a person of ordinary skill has good reason to pursue the known options within his or her technical grasp. If this leads to the anticipated success, it is likely that product [was] not of innovation but of ordinary skill and common sense. In that instance the fact that a combination was obvious to try might show that it was obvious under § 103.”KSR, 550 U.S. at ___, 82 USPQ2d at 1397. If any of these findings cannot be made, then this rationale cannot be used to support a conclusion that the claim would have been obvious to one of ordinary skill in the art. It is well within the skill of the organic chemist to recognize the fact that applicants claimed process is nothing but the combination of known individual chemical processes. Further, there is a reasonable a expectation of success that naphthalene dithiol may be purified using processes, such as crystallization, distillation, and column purification and can be made by teachings of the above cited prior art.
Therefore, it would have been obvious to one of ordinary skill in the art before the effective filing date of the claimed invention by taking advantage of the teaching of the above cited references and to make the instantly claimed process with a reasonable expectation of success. Modifying such parameters is prima facie obvious because an ordinary artisan would be motivated to develop an alternative process for economic reasons or convenient purposes from a known individual reaction steps, and to arrive at applicants’ process with a reasonable expectation of success, since it is within the scope to modify the process through a routine experimentation.
Response to Arguments
Applicants’ remarks and amendments, filed on 08/12/2026, have been considered but not found persuasive.
Applicant argued over Kim’s process of phenolic monomer as different from thiol of the instant claims. Applicant argued that applicant of the instant invention is the only company in the world at this time that commercially produce compound with purity of the instant claims 1 and has not sold to Kim. Applicant argued over older version of the product that was sold and was non-distilled.
This is not found persuasive and the instant claims stand rejected. This is because (1) Kim’s synthesis of unrelated compounds to 1,6-dithionaphthalene doesn’t preclude Kim’s teaching of using pure 1,6-dithionaphthalene in making resist underlayer film that applicant didn’t argue other than repeating the examples that office presented in the office action; (2) applicant only argued but provide no concrete evidence that applicant is the only one in the world selling it and Kim could not obtain purified form or Kim does not has ability to purify compounds, especially for using in resist underlayer film that demands pure compound.
Factors to be considered in determining whether a purified form of an old product is obvious over the prior art include whether the claimed chemical compound or composition has the same utility as closely related materials in the prior art, and whether the prior art suggests the particular form or structure of the claimed material or suitable methods of obtaining that form or structure. In re Cofer, 354 F.2d 664, 148 USPQ 268 (CCPA 1966) (Claims to the free-flowing crystalline form of a compound were held nonobvious over references disclosing the viscous liquid form of the same compound because the prior art of record did not suggest the claimed compound in crystalline form or how to obtain such crystals.). However, in the case of product-by-process claims, if a first prior art process is improved to enhance the purity of the product produced by the process, and if the purified product has no structural or functional difference from the products produced by other prior art processes, then the improvement in the first process that improves the purity of the product does not give rise to patentability. See Purdue Pharma v. Epic Pharma, 811 F.3d 1345, 117 USPQ2d 1733 (Fed. Cir. 2016).
Applicant argued over Rule over his broader teaching of aromatic nucleus besides naphthalene, such as 1,4-benzenedithiol and 2,6-dithionaphthalene and using processes, such as crystallization, solvent extraction and precipitation and not distillation. Applicant argued over purification selectivity of positional isomers. Applicant argued over comparative example 6 of distillation of 2,6-dithionaphthalene and problems because of sublimation and clogging and therefore nonobvious to use distillation as a procedure for purification.
This is not found persuasive and the instant claims stand rejected. This is because (1) Broader teaching of Rule does includes 1,6-naphtahlene dithiol and Rule does teach example of purification of 2,6-naphthalene dithiol. Further, a person of ordinary skill in the art would have been motivated to purify a crude compound using procedure, such as crystallization, precipitation, distillation, HPLC etc., as impurities are undesirable; (2) the office never mentioned anything about position isomers in relation to process for purification; (3) Based on the teachings of Rule, it would have been prima facie obvious to a person of ordinary skill in the art that crude naphthalene dithiol may be further purified using routine techniques such as precipitation, crystallization, distillation etc. It is also routine in the art that if the product cannot be crystallized or precipitated, the crude product may be purified using alternative procedures of purification, such as distillation and HPLC and vice versa.
Factors to be considered in determining whether a purified form of an old product is obvious over the prior art include whether the claimed chemical compound or composition has the same utility as closely related materials in the prior art, and whether the prior art suggests the particular form or structure of the claimed material or suitable methods of obtaining that form or structure. In re Cofer, 354 F.2d 664, 148 USPQ 268 (CCPA 1966) (Claims to the free-flowing crystalline form of a compound were held nonobvious over references disclosing the viscous liquid form of the same compound because the prior art of record did not suggest the claimed compound in crystalline form or how to obtain such crystals.). However, in the case of product-by-process claims, if a first prior art process is improved to enhance the purity of the product produced by the process, and if the purified product has no structural or functional difference from the products produced by other prior art processes, then the improvement in the first process that improves the purity of the product does not give rise to patentability. See Purdue Pharma v. Epic Pharma, 811 F.3d 1345, 117 USPQ2d 1733 (Fed. Cir. 2016).
Applicant is suggested to provide comparative data of unpredictable difference in properties of 1,6-naphthalene dithiol purified by crystallization vs distillation.
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.
Conclusion
No claim is allowed.
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/PANCHAM BAKSHI/Primary Examiner, Art Unit 1623
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