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 .
DETAILED ACTION
Claims 1, 3, 7-10, 16, 17, and 20-22 of T. Tatsumi et al., US 17/783,848 (Dec. 2, 2020) are pending and under examination and are rejected.
Claim Interpretation
Examination requires claim terms first be construed in terms in the broadest reasonable manner during prosecution as is reasonably allowed in an effort to establish a clear record of what applicant intends to claim. See, MPEP § 2111. During patent examination, the pending claims must be "given their broadest reasonable interpretation consistent with the specification. MPEP § 2111.
Interpretation of “an additive for preventing solidification of a reaction mixture and/or improving flowability of the reaction mixture”
Claim 1 as amended recites:
1 . . . comprising . . . an additive for preventing solidification of a reaction mixture and/or improving flowability of the reaction mixture . . .
The specification leaves the meaning of this limitation open; that is the specification teaches that:
[0017] The additive is not specifically limited as long as it prevents the solidification of the reaction mixture and/or improves the flowability and improves the stirring of the reaction mixture under the low temperature reaction conditions of the present invention. Examples of the additive include at least from surfactants, monohydric alcohols, dihydric alcohols (glycol), trihydric alcohols (glycerin), ether solvents, glycol ether solvents, carboxylic acid solvents, nitrogen solvents, sulfur solvents, and fluorine solvents. Preferred are surfactants, monohydric alcohols, dihydric alcohols, trihydric alcohols, ether solvents, and glycol ether solvents. Surfactants, monohydric alcohols, and dihydric alcohols are more preferable, and surfactants are even more preferable.
Specification at page 9, [0017]. The specification teaches that while benzidine rearrangement reactions were conventionally carried out at temperature from -10 to +80°C, in particular, in the vicinity of -10°C to 0°C, it has been discovered that the yield is improved by carrying out the benzidine rearrangement reaction under the low temperature conditions according to the present invention, whereby side reactions are suppressed to increase selectivity. Specification at page 8, lines 10-16.
The specification teaches that by carrying out the benzidine rearrangement reaction in the presence of the additive, it is possible to prevent increase in the viscosity of the reaction solution so as to avoid decrease in the flowability, and to prevent the solidification of the reaction solution so as to avoid difficulty in stirring in the low temperature conditions. Specification at page 8, lines 21-25. In sum, the specification teaches one of skill that a significant factor in such reactions is balancing temperature: where higher temperatures promote fluidization of the viscous reactant/product (thus promoting efficient stirring/mixing), but higher temperatures can be problematic in such a highly exothermic reaction regarding heat removal and selectivity. Applicant thus addresses this problem with the claimed “additive”, which is taught to function by lowering the reaction-mixture viscosity thereby allowing an otherwise highly exothermic and difficult-to-stir reaction, to be effectively stirred/mixed at lower temperatures. In other words, the specification teaches that the claimed exothermic benzidine rearrangement appears to have no trouble occurring within a broad temperature range as long as the reactants can be efficiently stirred together.
In view of the forgoing, the term “an additive for preventing solidification of a reaction mixture and/or improving flowability of the reaction mixture” is broadly and reasonably interpreted as any liquid additive (e.g., solvent)1 or art-recognized flowability improver (e.g., a surfactant), in addition to the already-present claim 1 elements. MPEP § 2111. This is consistent with the specification teachings.
The Claim 1 Recitation of “to thereby complete a benzidine rearrangement reaction” Is not a Interpreted as a Claim Limitation
Claim 1 is amended to recite “to thereby complete a benzidine rearrangement reaction” as follows:
Claim 1 . . . and stirring the mixture for a reaction time of 1 minute to 1 hour at a temperature from -70 °C to -11 °C
to thereby complete a benzidine rearrangement reaction to form the diaminobiphenyl compound represented by the formula (1) . . .
A significant issue is whether the claim 1 recitation of “to thereby complete a benzidine rearrangement reaction” is a claim limitation or merely a non-limiting intended result of carrying out the claim 1 steps as recited.
Claim scope is not limited by claim language that does not limit a claim to a particular structure. MPEP § 2111.04(I). A ‘whereby clause’ in a method claim is not given weight when it simply expresses the intended result of a process step positively recited. MPEP § 2111.04(I) (citing Hoffer v. Microsoft Corp., 405 F.3d 1326, 1329, 74 USPQ2d 1481, 1483 (Fed. Cir. 2005). As stated in the MPEP, the determination of whether clauses, such as “to thereby complete a benzidine rearrangement reaction” at issue, are claim limitations, depends on the specific facts of the case. MPEP § 2111.04(I).
Applicant argues that the above claim 1 language should be interpreted as a claim limitation that “requires that the benzidine rearrangement reaction be completed within 1 minute to 1 hour”. Reply (3/26/2026) at page 6 (emphasis added).2
However, for the following reasons, the term is not interpreted as a claim limitation because it does not alter the claim 1 structure, rather it simply expresses the intended result of the claim 1 process steps positively recited. MPEP § 2111.04(I).
Here, the chemical genera of formulae (1) and (2) are relatively narrow, as are the claimed temperature and time ranges. The only claim 1 structural variable that can be manipulated is the claimed “additive”. In this regard, as discussed above, the specification teaches that the additive identity is not overly important:
[0017] The additive is not specifically limited as long as it prevents the solidification of the reaction mixture and/or improves the flowability and improves the stirring of the reaction mixture under the low temperature reaction conditions of the present invention.
Specification at page 9, [0017] (emphasis added). Thus, the claim 1 recitation of “to thereby complete a benzidine rearrangement reaction” does not appear to be functional language that can be met or manipulated only by specific choice of the correct “additive”. MPEP § 2173.05(g). Rather the specification teaches that any art-recognized flowability improver (e.g., a surfactant) will give the intended claim 1 result of “to thereby complete a benzidine rearrangement reaction” within the claim 1 temperature/time parameters. This weighs against interpretation of “to thereby complete a benzidine rearrangement reaction” as a claim limitation, but rather is the expected result of employing any art-recognized flowability improver.
The specification teaches ten working examples (i.e., Examples 1-9 and Comparative Example 1) all directed to the same reactants and product. Specification at pages 14-20.
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Specification working Examples 3-9 are performed with a claimed “additive”, within the claim 1 time/temperature conditions. Specification at pages 15-21 (data in Table 1 at page 21). Table 1 at page 21. Specification Examples 1, 2, and Comparative Example 1 are performed without the claimed “additive”, each at a reaction time of five hours and each giving the same 97% conversation. Specification at pages 14-15 (Examples 1 and 2); Id. at pages 19-20 (Comparative Example 1).
Significantly, no specification example reaction was analyzed to determine whether a “to thereby complete a benzidine rearrangement reaction” had occurred at any intermediate time or even after the specified reaction time was complete. For instance, working Examples 1, 2, and Comparative Example 1 were not checked, for example, one hour into the total five-hour time to determine whether any starting 3,3'-bis(trifluoromethyl)hydrazobenzene remained. Rather, each of the working examples takes the reaction mixture directly to workup after the specified reaction time, and a percent yield, selectivity, and percent conversion is determined. See data in Table 1, page 21. Performance of the specification Examples in this manner makes sense because the specification implicates efficient stirring as the exothermic reaction’s driving force rather than temperature. This further weighs against interpretation of “to thereby complete a benzidine rearrangement reaction” as a claim limitation.
Withdrawal Claim Rejections 35 U.S.C. 112(a) -- New Matter
Rejection of claims 1, 3, 7-10, 16, 17, 20 and 21 under 35 U.S.C. 112(a) as failing to comply with the written description requirement is withdrawn in view of Applicant’s amendments.
Maintained 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.
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 AIA 35 U.S.C. 103(a) 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 non-obviousness.
Claims 1, 3, 7-10, 16, 17, and 20-22 are rejected under AIA 35 U.S.C. 103 as being unpatentable over H. Atago et al., JP 2007246427 A (2007) (“Atago”) in view of T. Namekata et al., JP 2008214203 A (2008) (“Namekata”) or these two reference in further view of N. G. Anderson, PRACTICAL PROCESS & RESEARCH DEVELOPMENT, 27-52, 81-111, 113-143 (2000) (“Anderson”).
H. Atago et al., JP 2007246427 A (2007) (“Atago”)
A Google machine translation of H. Atago et al., JP 2007246427 A (2007) (“Atago”) was attached to the previous Office action, referred to herein as “Atago-Google-MT”.3 Atago-Google-MT replaces the original version of Atago, because it is clearer and of better quality.
Atago teaches a process for producing a 4,4′-diaminobiphenyl derivative which is useful as a raw material for polymer materials, dyes, pigments, etc. Atago-Google-MT at page 2, [0001]. By reference to H. Shine et al., 103 Journal of the American Chemical Society, 955-956 (1981), Atago teaches that the subject reaction is a benzidine rearrangement. Atago-Google-MT at page 2, [0002]-[0003].
Atago teaches that the reactant and products are room temperature solids requiring dispersion forces to promote the reaction, as follows:
[0015] Since the raw material hydrazobenzene derivative, the resulting 4,4'-diaminobiphenyl derivative, or both are mostly solid at room temperature, it is desirable to perform stirring in order to rapidly proceed with the reaction of the present invention. However, since the irradiated ultrasonic waves have the effect of crushing and stirring the powder particles, there is an advantage in that the stirring means can be inexpensive and have a low stirring capacity.
Atago-Google-MT at page 5, [0015] (emphasis added). Atago further teaches that surfactants can be used to improve wetting of the raw material surface and increase reactivity. Atago-Google-MT at page 6, [0020].
In this regard, Atago teaches the following:
[0020] In the present invention, surfactants can be used to improve wetting of the raw material surface and increase reactivity. These surfactants can be either non-reactive cationic or nonionic surfactants. Examples of cationic surfactants include alkylamine salts and imidazolium salts. Examples of nonionic surfactants include those having a hydrophilic moiety such as polyoxyethylene, polyoxypropylene, polyoxyethylene-polyoxypropylene copolymer, or polyhydric alcohol, and a hydrophobic moiety such as linear or branched alkyl, aromatic, or aromatic alkyl. The hydrophilic and hydrophobic moieties may be in any combination, and the bond between them may be ether, ester, or amide, specifically alkyl polyoxyethylene ether, alkyl polyoxypropylene ether, or the like. These nonionic surfactants can be used alone or in combination.
Atago-Google-MT at page 6, [0020] (emphasis added).
With respect to the dispersion medium or reaction solvent, Atago teaches that:
[0022] Therefore, in the present invention, a dispersion medium or solvent can be used to increase the fluidity of the reaction system. Examples of the dispersion medium include water, dilute sulfuric acid, and dilute hydrochloric acid. Examples of the solvent include toluene, xylene, chlorobenzene, and dichloromethane. Two or more of these solvents can also be used in combination.
Atago-Google-MT at page 6, [0022] (emphasis added). Atago further teaches the use of a combination of solvent and surfactant as follows:
[0023] In the present invention, prior to the reaction, the above-mentioned dispersion medium may be added to the starting hydrazobenzene derivative to prepare a slurry, or the above-mentioned solvent may be added to the hydrazobenzene derivative to prepare a solution, and then an acid may be added to the solution to carry out the rearrangement reaction. When adding the dispersion medium or solvent to the hydrazobenzene derivative, a suitable surfactant may be added. Alternatively, the acid to which a surfactant has been added may be added to the hydrazobenzene derivative to carry out the rearrangement reaction.
Atago-Google-MT at page 6, [0023].
With respect to reaction temperature, Atago teaches:
[0016] The reaction temperature in the present invention varies depending on the raw materials, but a low temperature is preferred to suppress the by-production of azobenzene derivatives and monoamines due to the disproportionation reaction of hydrazobenzene derivatives, and the production of rearrangement by-products such as diphenyline derivatives and semidine derivatives. Specifically, a temperature of -40 to 100°C is preferred, and a temperature of -20 to 10°C is more preferred.
Atago-Google-MT at page 5, [0016] (emphasis added).
Atago Example 1-1 is schematically summarized by the Examiner below.
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Atago-Google-MT at pages 6-7, [0024]. Atago teaches the following experimental procedure for Equation (2) in Example 1-1 as follows:
[0024]
(Example 1-1)
A 30 ml four -tube ultrasonic transducer equipped with a stirrer, an ultrasonic vibration rod connected to an ultrasonic irradiation device (Sonifier II model 250 manufactured by Branson, also used in the following examples), a dropping funnel, and a thermometer was used.
A flask was charged with 8.0 g of 2,2'-dichlorohydrazobenzene, 6.78 g of 22.4 wt% sulfuric acid (aqueous solution, hereinafter the same), and 3.97 mg of Noigen (nonionic surfactant, EA-120, manufactured by Daiichi Kogyo Co., Ltd.).
While stirring to form a slurry, the mixture was irradiated with ultrasonic waves (frequency= 20 Hz, drive power= 150 W, discontinuous, with 0.1-second exposure and 0.9 second exposure pauses) from an ultrasonic vibrating rod. The temperature inside the flask was lowered to 10 °C in an ice bath.
While maintaining these conditions, 14.48 g of 61.3% sulfuric acid was added dropwise over 1 hour, and stirring and ultrasonic irradiation were continued for the next 4 hours.
Composition analysis of the unreacted raw materials remaining in the reaction system at this point by gas chromatography revealed that the yield of 3;3'-dichloro-4,4'-diaminobiphenyl was 56.3%.
Atago-Google-MT at pages 6-7, [0024] (emphasis added).
Note that the surfactant employed in Atago Example 1-1 (i.e., Noigen EA–120) is known in the art as a polyoxyethylene phenyl ether of the formula R-O-(CH2CH2O)n-H, wherein R is nonylphenyl, and n is 5. See e.g., M. Chihara et al. EP 0426942 (1990) (“Chihara”); see Chihara at page 5, lines 43-44; Id. at page 8, lines 15-18. Atago Example 1-1 does not meet the claim 1 structural limitation of:
Claim 1 . . . wherein X1 and X2 are, independently of each other, a group selected from the group consisting of a trifluoromethyl group and, optionally fluorinated, isopropyl, isobutyl, sec-butyl, tert-butyl and neopentyl groups . . .
Atago teaches working Example 5, where the reactant meets the instantly claimed chemical structure limitations of claimed formula (2) and claimed formula (1) of claim 1. Atago Example 5 is summarized by the Examiner below.
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Atago-Google-MT at page 9, [0034]. The Example 5 procedure is as follows:
[Example 5]
[0034]
A 30 ml four-neck flask equipped with a stirrer, an ultrasonic vibrating rod of an ultrasonic irradiation device, a dropping funnel, and a thermometer was charged· with 2.38 g of 3,3'-di(trifluoromethyl)hydrazobenzene and 13.52 g of toluene. The mixture was stirred and exposed to ultrasound (same conditions as in Example 1-1) until the temperature inside the flask was reduced to -20°C.
While maintaining these conditions, 14.1 g of 56% sulfuric acid was added dropwise over 1 hour, after which stirring and ultrasound exposure (same conditions as in Example 1-1) were continued for 2 hours.
Composition analysis of the unreacted raw materials remaining in the reaction system at this point by gas chromatography revealed that the yield of 2,2'-di(trifluoromethyl}-4,4'-diaminobiphenyl was 58.3%.
Atago-Google-MT at page 9, [0034] (emphasis added). Again, Atago Example 5’s reactant and product respectively meet the chemical structure limitations of claim 1 formulae (1) and (2), but does not include the claim 1 “additive”.
Differences Between Atago and the Claims
Claim Limitations Met by Atago
Under a § 103 analysis, Atago Examples 1-1 and 5 teach the claim 1 limitation of
1. . . comprising . . . stirring . . .at a temperature of from -70°C to -11 °C . . .
because the Example 5 temperature of -20 °C falls within the claimed range and the Example 1-1 temperature of -10 °C is close to the claimed range. A prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. MPEP § 2144.05(I).
Both Atago Example 1-1 (stirred for at least 4 hours) and Example 5 (stirred for at least 2 hours) meet the claim 1 limitation of:
1 . . . comprising . . . for a reaction time of 1 minute to 1 hour. . .
This is at least because claim 1 recites the transitional phrase “comprising”, which is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. MPEP § 2111.03. That is, the claim 1 transitional phrase “comprising” permits additional reaction time.
Claim Recitations not Met by Atago
Atago Example 1-1 differs in that it does not meet the claim 1 structural limitation of X1 and X2. But Atago Example 1-1 does meet the claim 1 element of “an additive for preventing solidification of a reaction mixture and/or improving flowability of the reaction mixture” (i.e., surfactant Noigen EA–120).
Atago Example 5’s reactant and product respectively meet the chemical structure limitations of claim 1 formulae (1) and (2), as well as (per above the claimed temperature). But Atago Example 5 differs from claim 1 it does not include the claim 1 element of “an additive for preventing solidification of a reaction mixture and/or improving flowability of the reaction mixture”.
With respect to the claim 1 recitation of “to thereby complete a benzidine rearrangement reaction”:
Claim 1 . . . and stirring the mixture for a reaction time of 1 minute to 1 hour at a temperature from -70 °C to -11 °C
to thereby complete a benzidine rearrangement reaction to form the diaminobiphenyl compound represented by the formula (1) . . .
it is not determinable by the Office whether or not the benzidine rearrangement reaction of either of Atago Example 1-1 or 5 was “complete” within the claim 1 time range of 1 minute to 1 hour. This is because no such analysis was made by Atago. Where, per footnote 2, “complete” is reasonably interpreted as requiring that all of the claimed reactant “diphenylhydrazine compound represented by the following formula (2)” is consumed (i.e., analytically undetectable).
Atago further differs because this reference does not teach the claim 1 isolation procedure of:
Claim 1 . . . followed by adding water to the reaction mixture to raise the temperature thereof, filtering and neutralizing the reaction mixture.
Atago does not teach workup or isolation of the product. This is because Atago is concerned with analysis of the crude reaction mixture to determine product amount.
T. Namekata et al., JP 2008214203 A (2008) (“Namekata”)
Namekata is cited here for teaching the following claim 1 limitation not taught by Atago:
Claim 1 . . . followed by adding water to the reaction mixture to raise the temperature thereof, filtering and neutralizing the reaction mixture.
An English-language machine language translation is attached as the second half of reference Namekata. Namekata thus consists of 12 total pages (including the English-language portion). Accordingly, this Office action references Namekata page numbers in the following format “xx of 12”.
In Example 1, Namekata teaches the following reaction, where the starting toluene layer of 3,3'-bis(trifluoromethyl)hydrazobenzene is first obtained by way of a zinc-mediated m-nitrobenzotrifluoride reaction. Namekata at page 9 of 12 (Example 1).
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Namekata at page 9 of 12 (Example 1).
Namekatas’ procedure for the above reaction is reproduced below, which teaches that the workup procedure involves adding water, raising the temperature to 70 °C, filtration and neutralization.
95.3 g of the toluene layer obtained by the reduction reaction was dropped into 90.3 g of a 50% aqueous sulfuric acid solution at 0 °C, and after the dropwise addition, the mixture was reacted at 0 °C. for 5 hours.
After the reaction, 38.5 g of water was added to the reaction mixture, the temperature was raised to 70 °C, the toluene layer was removed, and the aqueous layer was washed with 8.0 g of toluene. Thereafter, the pH of the aqueous layer was adjusted to 1.0 with a 35% aqueous sodium hydroxide solution, and the precipitated crystals were collected by filtration. The obtained crystals were added to water, adjusted to pH 12 with 35% aqueous sodium hydroxide solution, and extracted with toluene. The toluene layer was separated and concentrated and crystallized to separate 12.5 g of 2,2'-bis(trifluoromethyl)-4,4'diaminobiphenyl having a purity of 99. 9%. The yield based on m-nitrobenzotrifluoride was 42.1 %.
Namekata at page 9 of 12 (Example 1). In sum, Namekata teaches the claim 1 limitation of:
Claim 1 . . . followed by adding water to the reaction mixture to raise the temperature thereof, filtering and neutralizing the reaction mixture.
can be applied to the process of Atago simply as a workup/isolation procedure.
Secondary Reference N. G. Anderson, PRACTICAL PROCESS & RESEARCH DEVELOPMENT, 27-52, 81-111, 113-143 (2000) (“Anderson”)
Anderson teaches temperature optimization of reactions. Anderson at page 122 (VIII) et seq. Anderson teaches that in general, lower reaction temperatures are used to increase selectivity and to avoid side reactions. Anderson at page 122 (“VIII. SELECT REACTION TEMPERATURE”).
Obviousness Rationale
It is first noted that Atago teaches that a significant factor in such reactions is balancing temperature: where higher temperatures promote fluidization of the viscous reactant/product (thus promoting efficient stirring/mixing) but higher temperatures can be problematic in such a highly exothermic reaction regarding heat removal and selectivity. Atago at page 16 of 32, [0002]-[0005]. Atago addresses this problem by employing ultrasonic irradiation and/or a surfactant to assist in fluidization. Atago at page 18 of 32, [0009]. One of ordinary skill would understand that Atago’s promotion of mixing/fluidization (by employing ultrasonic irradiation and/or a surfactant) would permit lower reaction temperatures and shorter reaction times.4
Claims 1, 3, 7-10, 16, 17, and 20-22 are obvious for the following reasons. First one of ordinary skill is motivated to perform Atago Example 5 by including a surfactant, thereby meeting the claim 1 limitation of “an additive for preventing solidification of a reaction mixture and/or improving flowability of the reaction mixture” (for instance, the Noigen surfactant employed in Atago Example 1-1 or any of those listed in [0020]), because Atago specifically teaches that a surfactant may be used in addition to a solvent in order to improve the wettability of the surface of the raw material and enhance the reactivity and that as such a surfactant, a cationic surfactant or a nonionic surfactant, both of which are nonreactive, can be used. Atago-Google-MT at page 6, [0020]; see also, Atago-Google-MT at page 6, [0023] (“When adding the dispersion medium or solvent to the hydrazobenzene derivative, a suitable surfactant may be added”).
One of ordinary skill is further motivated to practice Atago Example 5 (modified with a surfactant as proposed above), within the claimed temperature ranges:
Claim 1 . . . “at a temperature of from -70 °C to -11 °C”
Claims 7/16 . . . “at a temperature of from -55 °C to -50 °C”
Claim 22 . . . “at a temperature of from -70 °C to -45 °C”
This is because Atago teaches the following temperature ranges:
Specifically, a temperature of -40 to 100°C is preferred, and a temperature of -20 to 10°C is more preferred.
Atago-Google-MT at page 5, [0016] (emphasis added). Atago’s temperature ranges overlap with the claim 1 range and are close to the claim 7, 16, and 22 temperature ranges5. Further, one of ordinary skill is motivated to optimize to lower temperatures because Atago teaches one of ordinary skill that relatively low temperature to suppress heat generation and increase selectivity for the target product.
[0002] . . . This production method is described, for example, in the following Non-Patent Document 1.6 In this production method, the reaction is carried out at a relatively low temperature to suppress heat generation and increase selectivity for the target product.
Atago-Google-MT at page 2, [0002] (emphasis added).
[0016] The reaction temperature in the present invention varies depending on the raw materials, but a low temperature is preferred to suppress the by-production of azobenzene derivatives and monoamines due to the disproportionation reaction of hydrazobenzene derivatives, and the production of rearrangement by-products such as diphenyline derivatives and semidine derivatives. Specifically, a temperature of -40 to 100°C is preferred, and a temperature of -20 to 10°C is more preferred.
Atago-Google-MT at page 5, [0016] (emphasis added). Thus, the claimed temperature limitations are not a patentable distinction because reaction temperature is recognized by Atago as a result-effective variable and the instant specification indicates no criticality with respect to the claimed temperature ranges.7 MPEP § 2144.05(II) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955)), see specification at page 5, lines 15-20; Id. at page 6, lines 1-5; Id. at page 8, lines 1-16. In sum, one of ordinary skill is motivated to perform Atago Example 5 at the claimed lower temperature ranges (depending upon the specific, reactant, solvent or additive employed), to increase selectivity and to avoid side reactions as taught by Anderson and Atago. Anderson at page 122 (“VIII. SELECT REACTION TEMPERATURE”).
Finally, as noted above, practice of Atago Example 5 as proposed above already meets the claim 1 limitation of:
1 . . . comprising . . . for a reaction time of 1 minute to 1 hour. . .
by way of Atago’s Example 5 step of “which stirring and ultrasound exposure (same conditions as in Example 1-1) were continued for 2 hours”. This is at least because claim 1 recites the transitional phrase “comprising”, which is inclusive or open-ended and does not exclude additional, unrecited elements or method steps. MPEP § 2111.03. That is, claim 1 transitional phrase “comprising” permits additional reaction time over the recited “of 1 minute to 1 hour”. For example, during the first minute of Atago Example 5, which is per claim 1 “a reaction time”, Atago’s reaction produces the claimed product. This limitation is therefore clearly met by Atago.
With respect to the claim 1 recitation of “to thereby complete a benzidine rearrangement reaction”:
Claim 1 . . . and stirring the mixture for a reaction time of 1 minute to 1 hour at a temperature from -70 °C to -11 °C
to thereby complete a benzidine rearrangement reaction to form the diaminobiphenyl compound represented by the formula (1) . . .
it is not determinable by the Office whether or not the benzidine rearrangement reaction of either of Atago Example 1-1 or 5 was “complete” within the claim 1 time range of 1 minute to 1 hour. However, this recitation does not distinguish over Atago because as discussed in Claim Interpretation above, “to thereby complete a benzidine rearrangement reaction” is not interpreted as a claim limitation because it does not alter the claim 1 structure, rather it simply expresses the intended result of the claim 1 process steps positively recited. MPEP § 2111.04(I). Alternatively, this recitation is inherently met by practice of Atago Example 5 as proposed above. For instance, practice of Atago Example 5 modified by adding Noigen surfactant (a non-ionic surfactant) as employed in Atago Example 1-1 as proposed is essentially the same reaction as specification working Examples 3 and 4, which were stopped and worked up after five minutes. See specification at page 21, Table 1. When the examiner "has reason to believe" that the prior art reference inherently teaches the functional limitation, the burden shifts to the patent applicant to show that the functional limitation cannot be met by the prior art reference. MPEP 2112(V), see also, In re Schreiber, 128 F.3d 1473, 1478 (Fed. Cir. 1997); In re Chudik, 674 F. App'x 1011, 1012 (Fed. Cir. 2017) (both citing In re Swinehart, 439 F.2d 210, 212, 58 C.C.P.A. 1027 (C.C.P.A. 1971)).
Finally, the claim 1 limitation of:
Claim 1 . . . followed by adding water to the reaction mixture to raise the temperature thereof, filtering and neutralizing the reaction mixture.
is obvious because Namekata teaches one of ordinary skill that this claim step can be applied to the process of Atago simply as a workup/isolation procedure. The above proposed modification of Atago meets each and every limitation of claims 1, 3, 7-10, 16, 17, and 20-22
Each and every limitation of claim 3 is clearly met by the above proposed modification of Atago Example 5, wherein the X1 and X2 in the formulas (1) and (2) are trifluoromethyl groups.
The claim 7, 16 and 22, narrower temperature ranges were discussed in detail above.
Claims 8-10, 17 and 20 are obvious because one of ordinary skill is motivated to employ the surfactant employed in Atago Example 1-1 (i.e., Noigen EA–120) in Atago Example 5, which is known in the art as a polyoxyethylene phenyl ether of the formula R-O-(CH2CH2O)n-H, wherein R is nonylphenyl, and n is 5. See e.g., M. Chihara et al. EP 0426942 (1990) (“Chihara”); see Chihara at page 5, lines 43-44; Id. at page 8, lines 15-18. Noigen EA–120 is thus (per claims 8, 17 and 20) a “surfactant” or “monohydric alcohol”; and is (per claims 9 and 10) a non-ionic surfactant.
The further limitations of claim 21:
21. The method according to claim 1, wherein the benzidine rearrangement reaction is carried out in the presence of the additive for a reaction time of 3 to 10 minutes at the temperature according to claim 1.
are met for the reasons discussed in detail above.
Applicant’s Argument
Applicant argues that the cited combination of prior art references at least fails to disclose or suggest a benzidine rearrangement reaction which is completed within 1 minute to 1 hour and thus does not meet (per claim 1) “to thereby complete a benzidine rearrangement reaction”:
Claim 1 . . . and stirring the mixture for a reaction time of 1 minute to 1 hour at a temperature from -70 °C to -11 °C
to thereby complete a benzidine rearrangement reaction to form the diaminobiphenyl compound represented by the formula (1) . . .
Reply at page 6. Applicant states that in Atago, all of the examples add acid over a period of one hour; however, the reaction is not completed in one hour. Reply at page 6.
This argument is not persuasive because “to thereby complete a benzidine rearrangement reaction” does not distinguish over Atago because as discussed in Claim Interpretation above, it is not interpreted as a claim limitation because it does not alter the claim 1 structure, rather it simply expresses the intended result of the claim 1 process steps positively recited. MPEP § 2111.04(I). Alternatively, for the reasons discussed in detail above, this recitation is inherently met by practice of Atago Example 5 as proposed above.
This argument is not persuasive for the following additional reasons. It is not at all clear, as argued by Applicant, that Atago Examples 1-1 and 5 were not “complete” (see footnote 2) within the claim 1 time ranges. Atago provides no information regarding whether the starting material was completely consumed at any time point. Rather Atago Example 5 performs “a composition analysis of the unreacted raw materials remaining in the reaction system at this point [after two hours] by gas chromatography revealed that the yield of [product] 2,2'-di(trifluoromethyl}-4,4'-diaminobiphenyl was 58.3%”. Atago-Google-MT at page 9, [0034]. Similarly, none of the instant specification working examples provide any information regarding how much, if any, staring material remains during the time-course of, or after stopping the reaction for workup. See e.g., Specification Example 4 at page 14. Here, Atago may very well be “complete” before one hour; conversely the specification working Examples 4 may or may not be complete after the five-minute reaction time. See Specification at page 21, Table 1.
Applicant argues that in Atago, each of these reactions is carried out at a temperature of + 10°C, over 20 degrees warmer than the maximum reaction temperature now recited in Claim 1. Reply at page 6.
This argument is not persuasive because Atago teaches an Example 5 temperature of -20 °C, which falls within (and anticipates) the claimed range and the Atago Example 1-1 temperature of -10 °C is close to the claimed range. A prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. MPEP § 2144.05(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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ALEXANDER R. PAGANO
Examiner
Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 Prior art elements should not be double counted as claim elements; for example, the claim 1 “an organic solvent” is also a claimed additive, however this element is already accounted for in claim 1. Becton, Dickinson & Co. v. Tyco Healthcare Group, LP, 616 F.3d 1249, 95 USPQ.2d 1752 (Fed. Cir. July 29, 2010). Thus, a prior art reference teaching a reaction mixture comprising two different solvents would meet the claim 1 limitations of solvent and an additive.
2 Absent a specification definition of “complete”, this term is reasonably interpreted by the Examiner, in view of its plain meaning, as requiring that all of the claimed reactant “diphenylhydrazine compound represented by the following formula (2)” is consumed (i.e., analytically undetectable) within the claimed time and temperature conditions. MPEP § 2111. This interpretation is reasonable and consistent with the specification working Examples 3-9. These examples are performed with a claimed “additive”, within the claim 1 time/temperature conditions. Specification at pages 15-21 (data in Table 1 at page 21). Table 1 at page 21. However, the percent yields in each of Examples 3-9 hover around 50% yield. Thus, the specification teaches that, under claim 1, not all of the starting formula (2) ends up as benzidine rearranged product.
3 The Google translation webpage at https://translate.google.com/?sl=ja&tl=en&op=translate was used by the Examiner to translate images of H. Atago et al., JP 2007246427 A (2007) into English.
4 The focus when making a determination of obviousness should be on what a person of ordinary skill in the pertinent art would have known at the relevant time, and on what such a person would have reasonably expected to have been able to do in view of that knowledge. This is so regardless of whether the source of that knowledge and ability was documentary prior art, general knowledge in the art, or common sense. MPEP § 2141(II).
5 In the case where the claimed ranges "overlap or lie inside ranges disclosed by the prior art" a prima facie case of obviousness exists. MPEP § 2144.05(I). Similarly, a prima facie case of obviousness exists where the claimed ranges or amounts do not overlap with the prior art but are merely close. MPEP § 2144.05(I).
6 Atago cites H. Shine et al., 103 Journal of the American Chemical Society, 955-956 (1981) as patent document 1. Atago-Google-MT at page 2, [0003]
7 It is a well-settled tenet that one of ordinary skill in the art to develop workable or optimum ranges for result-effective parameters, where Applicant can rebut a prima facie case of obviousness by showing the criticality (unexpected result) of the range. MPEP § 2144.05; see also, In re Boesch, 617 F.2d 272,276 (CCPA 1980); In re Aller, 220 F.2d 454, 456 (CCPA 1955) (generally, differences in concentration or temperature will not support the patentability of subject matter encompassed by the prior art unless there is evidence indicating such concentration or temperature is critical); In re Woodruff, 919 F.2d 1575, 1578 (Fed. Cir. 1990) (explaining that, in cases in which the difference between the claimed invention and the prior art is some range or other variable within the claims, "the applicant must show that the particular range is critical, generally by showing that the claimed range achieves unexpected results relative to the prior art range"). To establish unexpected results over a claimed range, applicants should compare a sufficient number of tests both inside and outside the claimed range to show the criticality of the claimed range. MPEP § 716.02(d) (citing In re Hill, 284 F.2d 955, 128 USPQ 197 (CCPA 1960).
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