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 1,3,9-11,13,15-17 and 24 of E. Auyeung, et al. US 18/004,707 (01/09/2023) are pending, and under Restriction and Election requirement. Claims 16-17 and 24 are withdrawn as not read on the elected Group/species. Claims 1,3,9-11,13 and 15 are under examination on merits and are rejected.
Election/Restrictions
Pursuant to the restriction requirement, Applicant elected Group 1 (claims 1,3,9-11, 13 and 15), without traverse, during the phone interview held on 08/19/2025. Claims 16-17 and 24 drawn to non-elected Group (II)-(III) are withdrawn from consideration pursuant to 37 CFR 1.142(b). Given Applicant did not provide any traversal in the reply filed on 12/17/2025, the Restriction is made as Final.
Pursuant to the election of species requirement, Applicant elected, without traverse, “the mixture of anilines comprises 4-n- butylaniline and 4-methylaniline” as the species, during the phone interview held on 08/19/2025, for prosecution on the merits to which the claims shall be restricted if no generic claim is finally held to be allowable. Claims 1,3,9-11, 13 and 15 read on the elected species. The elected species was determined to be unpatentable for the reason as discussed in the 103 rejection below. The provisional species election requirement is in effect.
Claim Interpretation
During examination, a claim must be given its broadest reasonable interpretation consistent with the specification as it would be interpreted by one of ordinary skill in the art. MPEP § 2173.01(I); § 2111.01. Under a broadest reasonable interpretation, words of the claim must be given their plain meaning, unless such meaning is inconsistent with the specification. The plain meaning of a term means the ordinary and customary meaning given to the term by those of ordinary skill in the art at the time of the invention. MPEP § 2173.01(I).
Interpretation of the Claim Term “R-anilines”
Claim 1 recites the claim term “R-anilines” in the following context:
1. A method of making 1,4,5,8-tetrakis(R- phenylamino)anthracene-9,10-dione comprising the step of contacting 1,4,5,8- tetrachloroanthraquinone with a mixture of R-anilines comprising at least two different anilines, under conditions to produce 1,4,5,8-tetrakis(R-phenylamino)anthracene-9,10-dione, where each R is independently a linear, branched, or cyclic hydrocarbons having from 1 to 20 carbon atoms, and may be located in the para, meta, or ortho position (relative to the aniline N- atom).
The specification discloses the related information as follows:
The present disclosure provides a 1,4,5,8-tetrakis(R- phenylamino)anthracene-9,10-dione characterized by having at least two different R groups. The desired product therefore corresponds to the following formula, . . . ..
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. . . ..
. . . .. The mixture of anilines can comprise unsubstituted aniline and/or one or more mono, di, or tri hydrocarbyl substituted anilines, where the hydrocarbyl substituted group can independently be any C1 through C20 linear, branched, or cyclic hydrocarbyl group. The mixture of anilines may comprise more than 2 different anilines. . . .
Specification at pages 2, line 19 to page 3, line 15; emphasis added.
According to its plain meaning and consistent with the structure of the product disclosed in the specification, the claim term “R-anilines” is broadly and reasonably interpreted as a type of compounds having the following chemical structure:
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Wherein, R is hydrogen or linear, branched, or cyclic hydrocarbons having from 1 to 20 carbon atoms, and the numbers of R in one aniline can be 1, 2 or 3.
Interpretation of the Claim Language “each specific aniline in the mixture of R-anilines is present in in an amount within 10% molar amounts of all other anilines in the mixture”
The instant claim 1 recites the limitation of:
. . . ; and wherein each specific aniline in the mixture of R-anilines is present in in an amount within 10% molar amounts of all other anilines in the mixture.
Applicant has the follows argument in the Remarks filed on 12/17/2025:
The Examiner has stated that Omaya teaches that Omaya's description that Example 11 was synthesized in the "same manner", suggesting that means that the amount of p- toluidine and 4-cyclohexylaniline should be the same (i.e. 54.35 parts), but there is no indication that these anilines should be added in equal amounts, and in fact, as the target compound of Omaya has only 1 group resulting from 4-cyclohexylaniline versus 3 from the - toluidine, it would be expected that these materials should be used in a 1:3 ratio. Thus, it would not be obvious to use a reaction mixture of these two materials in the range of 40-60% as now required by claim 1 for a 2-component aniline mixture.
Remarks at page 4 last paragraph to page 5, paragraph 1, emphasis added.
Consistent with Applicant’s argument, the claim language “ each specific aniline in the mixture of R-anilines is present in in an amount within 10% molar amounts of all other anilines in the mixture” is broadly and reasonably interpreted as the molar ratio between each of the anilines in the reaction mixture is in a range of 0.9 to 1.1.
Drawing Objections
The drawing field on 09/01/2023 is objected to because “[W]here only a single view is used in an application to illustrate the claimed invention, it must not be numbered and the abbreviation "FIG." must not appear” See MPEP 608.02 V (u).
Withdrawal Claim Rejections - 35 USC § 112
Rejection of claim 13 is rejected under 35 U.S.C. 112(b) as indefinite for the recitation of “an organic solvent which is above the boiling point of the organic solvent” is withdrawn in view of the amendment makes the instant claim 13 definite.
Withdrawal Claim Rejections - 35 USC § 102
Rejection of claims 1, 9-11, 13 and 15 under 35 U.S.C. 102 (a)(1) as being anticipated by T. Oyama, et al, JP01129068A (1989)(“Oyama”) is withdrawn because the limitation of “wherein each specific aniline in the mixture of R-anilines is present in in an amount within 10% molar amounts of all other anilines in the mixture.” in the instant claim 1 can not be met by Oyama.
Withdrawal Claim Rejections - 35 USC § 103
Rejection of claim 3 and the elected species are rejected under 35 U.S.C. 103 as being unpatentable over Oyama is withdrawn for the same reason as given above.
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 for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claims 1,3,9-11,13, 15 and the elected species are rejected under 35 U.S.C. 103 as being unpatentable over a combination of O. Tsukasa, et al and N. Ito, et al, JPS61291651A (1986)(“Ito”).
O. Tsukasa, et al, EP0323184A1 (1989)
Tsukasa teaches a 1,4,5,8-tetraanilidoanthraquinone represented by the formula (I) which is a selective optical filter in the near infrared region and at least one of whose anilido benzene rings bears a halogen atom.
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Tsukasa at page 2, line 25-44.
Tsukasa teaches that:
The anthraquinones represented by the formula (I) given hereinbefore are preferably prepared by reacting pure, i.e., of at least 95% and more preferably at least 99% purity, 1,4,5,8-tetrachloroanthraquinone, e.g., recrystallized from a solvent such as monochloro-benzene, dichlorobenzene, nitrobenzene or the like, with aniline derivatives represented by the formula (V), (VI), (VII) and (VIII)
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wherein A, B, C and D correspond to A, B, C and D of formula (I). These reagents are reacted in the molar ratio of the anthraquinone to the aniline derivatives of formulae (V) to (VIII) employed in the reaction of at least 1:4, in the presence of a catalytically effective amount of copper ions, a salt of an aliphatic carboxylic acid and a benzyl alcohol derivative which may bear any substituent.
Tsukasa at page 3, line 16-36, emphasis added.
Tsukasa teaches that:
Examples of the salt of an aliphatic carboxylic acid which may be used in the preparation of a halogenated 1,4,5,8-tetraanilidoanthraquinone according to the present invention, to neutralize the hydrogen halide produced in the reaction, include alkali metal salts of lower fatty acids, sodium formate, sodium acetate, potassium acetate and potassium propionate, and of these, potassium acetate is particularly preferable. The molar amount of the salt of an aliphatic carboxylic acid used is 1 to 10 times, preferably 2 to 5 times that of the 1,4,5,8--tetrachloroanthraquinone.
Tsukasa at page 3, line 36-42, emphasis added.
Tsukasa teaches that:
The copper ions used as the catalyst can be supplied from any source, e.g., a copper salt of any organic or inorganic acid which forms copper ions in the reaction mixture. They are preferably supplied, however, by copper sulfate. The molar amount of the source of the copper ions used can vary widely but suitably is 0.1 to one times that of 1,4,5,8-tetrachloroanthraquinone.
In the preparation of an anthraquinone according to the present invention, the aniline derivatives acc-ording to formulae (V) to (VII) are reacted with 1,4,5,8-tetrachloro-anthraquinone in a molar ratio of the former to the latter of at least 4:1.
They preferably are reacted with each other with stirring in the presence of the above-mentioned copper ions, salt of an aliphatic acid and benzyl alcohol derivative using the aniline derivatives as the solvent, although a separate solvent such as ethyl cellosolve or the like can be employed. The usual amount of solvent is 15 to 20 times the molar amount of anthraquinone.
Tsukasa at page 3, line 49-57, emphasis added.
Tsukasa also teaches that:
The reaction is conducted at an elevated temperature, e.g., 80 to 170°C, preferably 100 to 150°C. When the reaction temperature is higher than 170°C, the desired product is liable to decompose and when it is lower than 80°C, unreacted starting materials tend to remain. A reaction period of 5 to 10 hours is usually enough for the reaction to go to completion.
Tsukasa at page 4, line 2-5, emphasis added.
Tsukasa teaches working Examples, such as Example 1 as follows:
Example 1
A mixture of 10.87 parts of 99%-purity 1,4,5,8--tetrachloroanthraquinone recrystallized from chloro-benzene, 27.2 parts of p-toluidine, 31.3 parts of p-chloroaniline, 13.4 parts of potassium acetate, 1.24 parts of copper sulfate and 3.41 parts of benzyl alcohol was heated to 130°C under a nitrogen gas flow and the reaction mixture was then maintained at this temperature for 6.5 hours. Afterward the reaction mixture was cooled to 70°C and was then poured into 217 parts of ethanol, followed by filtration, ethanol washing, water washing and drying. The resultant crude product was then subjected to recrystallization from pyridine, thereby obtaining 14.2 parts of the desired 1-(p-chloroanilido)--4,5,8-tris(p-methylanilido)anthraquinone (yield = 70%) in high purity. By the use of high-speed liquid chromatography (made by Shimadzu Seisakusho Ltd., SHIM-PACK CLC-ODS column, acetonitrile development, detection at 254 nm), it was confirmed that the purity of the product was 99.5%. . . ..
Tsukasa at page 4, Examples 1-2, Emphasis added.
Examiner schematically summarized the Tsukasa Examples such as Example 1 as follows:
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To summarize, Tsukasa teaches a method for preparation of 1,4,5,8-tetraanilidoanthraquinone comprising at least two different aniline moieties through reacting of 1,4,5,8--tetrachloroanthraquinone with at least two different anilines in the presence of a base and a copper catalyst.
The Tsukasa method of preparation 1,4,5,8-tetraanilidoanthraquinone compound in Example 1 comprise:
(i). contacting 1,4,5,8- tetrachloroanthraquinone with a mixture of R-anilines comprising at least two different anilines, wherein each R locates at para position relative the NH2; and
(ii). reaction is conducted at a condition to produce 1,4,5,8-tetrakis(R- phenylamino)anthracene-9,10-dione.
Difference between Tsukasa and the Claims
The Tsukasa method differs from the instant claim 1 only in that the Cl atom in p-chloroaniline is not a alky group which different with methyl group.
N. Ito, et al, JPS61291651A (1986)(“Ito”)
Note: Ito is published in Japanese, a copy of machine translation is attached as the second party resulting the total page of the reference is 11 and the format for recitation of the reference is xx/11.
Ito teaches a dye having a general formula (I) which can be used in a color filter substrate.
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wherein benzene nuclei A, B, C, and D are the same or each independently may be substituted with a lower alkyl group, a cycloalkyl group, a lower alkoxy group, a trifluoromethyl group, or a halogen atom.
Ito at page 6/11, 2. Scope of claims, 1-3.
Ito also teaches a method of preparation of the dye having a general formula (I) by contacting of Leuco-1,4,5,8-tetrahydroxyanthraquinone with at least four moles of aniline derivatives (II)-(IV) in the presence of mineral acid, boric acid and zinc.
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Ito at page 7/11, 3. Detailed Description of the Invention.
Ito teaches working example for synthesis of the dye general formula (I) such as the compounds in Example 1 and Example 8 that is synthesized in the same manner as the synthesis of example compound A.
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Ito at page 9/11 for example A and 10/11-11/11 for Example 8.
Regarding the preparation of compound A in Example 1, Ito teaches that:
The dye of formula (A) above was prepared by mixing leucine-1,4,5,8-tetrahydroxyanthraquinone 24g1, toluidine 150g, boric acid 5g, 35% hydrochloric acid 10g, and zinc 2g, and reacting at 150°C for 5 hours. After the reaction, the mixture was cooled to 80°C, poured into 500mℓ of methanol, filtered, washed, and dried to obtain compound 40g of formula (A) above.
Ito at 9/11, Example-1 and 3/11, Example-1.
Therefore, Ito fairly teaches one skilled artisan that the Example 8 compound is prepared in the following method:
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The Ito method of preparation of Example 3 comprise:
(i). contacting 1,4,5,8-tetrahydroxyanthraquinone with a mixture of R-anilines comprising at least two different anilines, wherein each R is independently a linear hydrocarbons having from 1 to 20 carbon atom and locates at para or ortho position relative the NH2; and
(ii). reaction is conducted at a condition to produce 1,4,5,8-tetrakis(R- phenylamino)anthracene-9,10-dione.
Difference between Ito and the Claims
The Ito method differs from the instant claim 1 only in that the leuco-1,4,5,8-tetrahydroxyanthraquinone is not the claimed 1,4,5,8--tetrachloroanthraquinone. However, after comparing the chemical structures of the Ito Example 8 compound and the Tsukasa 1,4,5,8-tetraanilidoanthraquinone in Tsukasa Example 1, one ordinary skilled artisan would be appraised that the Ito Example 8 compound can also be prepared from1,4,5,8--tetrachloroanthraquinone with the method taught by Tsukasa.
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Obviousness Rational of the Claims 1, 9-11, 13 and 15
Claim 1 is obvious because one ordinary skilled artisan seeking the Ito Example 8 compound for a color filter substrate is motivated to use the Tsukasa method with 1,4,5,8-tetraanilidoanthraquinone and equal molar amounts of specific anilines as starting materials the as indicated below, thus arrive at a method meeting each and every limitation of claim 1, therefore, claim 1 is obvious.
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One ordinary skilled artisan is motivated to do so and with a reasonable of success because:
(i). Tsukasa teaches that 1,4,5,8-tetraanilidoanthraquinone comprising at least two different aniline moieties can be prepared through reacting of 1,4,5,8--tetrachloroanthraquinone with at least two different anilines in the presence of a base and a copper catalyst; and
(ii). compared to the Ito method, the Tsukasa method is conducted at a mild condition such as at lower temperature (150°C vs 130°C) and without strong acids (boric acid and 35% hydrochloric acid).
The rational supporting the motivation is “simple substitution of one known element for another to obtain predictable results”. See MPEP 2143 I (B). One ordinary skilled artisan is also motivated to use equal molar amounts of 4-butylaniline and 4-propylaniline because they have the same number of reaction sites in the Ito Example 8 compound.
Claims 9-11 are obvious because the above proposed method is conducted in the presence of potassium acetate as a base and copper sulfate as a catalyst.
Claim 13 is obvious because one ordinary skill is also motivated to further modify the proposed method by using ethyl cellosolve as the solvent and the optimize the reaction temperature. One ordinary skill has a motivation to do these modification as Tsukasa teaches that a separate solvent such as ethyl cellosolve or the like can be employed for his method and the reaction can be conducted preferably at 100 to 150°C. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation. MPEP § 2144.05(II) (citing In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955).
Claim 15 is obvious because Tsukasa teaches to filtrate and wash with the final product with ethanol and water.
Obviousness Rational of the Claim 3 and the elected species
As mentioned above that the combination of Ito and Tsukasa teaches a method meeting each and every limitation of claim 1.
The combination differs from claim 3 and the elected species only in that the combination does not teach a mixture of aniline comprises 4-n-butylaniline and 4-methylaniline.
Obviousness of a claimed compound can also be supported where there is motivation to substitute particular chemical moieties in a prior art compound for others so as to arrive at a claimed compound. MPEP § 2143(I)(B). For example, in the pharmaceutical arts, the rational is stated as motivation to select a known compound and also motivation to structurally modify the selected compound in a particular way to achieve a claimed compound. MPEP § 2143(I)(B) (see for example, MPEP § 2143(I)(B) Example 9, citing Eisai Co. Ltd. v. Dr. Reddy’s Labs., Ltd., 533 F.3d 1353, 87 USPQ2d 1452 (Fed. Cir. 2008).
One of ordinary skill is motivated to select the Ito Example 8 compound for further investigation because Ito teaches that it is an example of the general formula (I) and it has good filter properties and properties as an optical recording medium. Having selected the Ito Example 8 compound, one of ordinary skill is motivated to modify it by replacing 4-propylaniline with 4-methylaniline as indicated below:
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One ordinary skill is motivated to do this modification with a reasonable expectation of success because Ito teaches that the benzene nuclei A, B, C, and D can be the same or each independently a lower alkyl group and the rational supporting the modification is “obvious to try” that is choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success. MPEP 2143. I (E). One ordinary skill is further motivated to do the proposed modification because the Ito Example 1 compound A comprises 4-methylaniline.
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One ordinary skill is further motivated to prepare the proposed compound with the method taught by Tsukasa as indicated below, thus arrive at a method meeting each and every limitation of claim 3 and the elected species , therefore, claim 3 and the elected species are obvious.
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Applicant’s Arguments
Applicant argues on the ground that there is no motivation to use same molar amounts of different anilines to prepare the prior art compound or the proposed compound. Remarks at page 4 last paragraph to page 5, last paragraph.
These arguments have been fully considered but not persuasive. As discussed above in the rejection that Ito Example 8 compound comprises the same molar amount of (4-butylphenyl)amino and (4-propylphenyl)amino, therefore, one ordinary skill has a motivation to use same molar amount of 4-butylaniline and 4-propylaniline to react with 1,4,5,8-tetraanilidoanthraquinone as proposed.
Conclusion
THIS ACTION IS MADE FINAL. 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.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to FRANK S. HOU whose telephone number is (571)272-1802. The examiner can normally be reached 6:30 am-2:30 pm Eastern on Monday to Friday.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Scarlett Goon can be reached at (571)2705241. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/FRANK S. HOU/Examiner, Art Unit 1692
/ALEXANDER R PAGANO/Primary Examiner, Art Unit 1692
1 The translation translated “g” into “9” and 35% into 356.