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 Claims
Claims 9-22 are currently pending and under examination.
Priority
The instant application 18/717,185 filed on June 6, 2024 is a 371 of PCT/TR2021/051541 filed December 28 2021.
Information Disclosure Statement
The information disclosure statement (IDS) submitted on 06/6/2024. The submission is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement is being considered by the examiner.
Claim Objections
Claims 1-6 objected to because of the following informalities:
Claims 1-6 are objected to because the claims inconsistently recite plural “optical brighteners.” The claims should be amended to recite the singular optical brightener.
Claim 3 recites “between 220 to 270°C.” This should be corrected to:
between 220°C and 270°C.
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 (i.e., changing from AIA to pre-AIA ) 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, 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 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 1–6 are rejected under 35 U.S.C. §103 as being unpatentable over Ma (CN102070627A) in view of Wang (US5332828A, referred to herein as “Wang‘828’”), further in view of Krull (US20100076040A1), Wang et al. (CN112094189A, referred to herein as “Wang‘189”), and Kimura et al. (EP1674459A1).
Ma teaches a method for preparing 2,5-bis(5-tert-butyl-2-benzoxazolyl)thiophene(see p. 1, (54)), which corresponds to the first benzoxazole-based optical brightener of claim 4. Ma teaches that placing the starting materials in a reaction vessel including thiophene-2,5-dicarboxylic acid, p-tert-butyl-o-aminophenol, and boric acid, and carrying out condensation, dehydration, distillation, and refinement to produce the target thiophene-bisbenzoxazole optical brightener(see p. 1, (57), Claims). Ma further teaches that the reaction reaches about 230°C(see claim page, claim 1, (2) dehydration)(which falls within the claimed temperature range of 220°C –270°C). Thus, Ma teaches the reactor vessel, thiophene-2,5-dicarboxylic acid, p-tert-butyl-o-aminophenol, and boric acid catalyst, dehydration- condensation reaction, temperature, and first bisbenzoxazole-based optical brighter limitations.
Ma does not teach the second benzoxazole-based optical brightener of claim 5, 4,4'-Bis(2-benzoxazolyl)stilbene, nor does Ma teach the use of stilbene-4,4'-dicarboxylic acid and 2-aminophenol to produce the stilbene- bisbenzoxazole product. Ma also does not teach liquid paraffin placed in the reactor vessel with the acid and catalyst.
Wang‘828 teaches a process for preparing 4,4′-bis(2-benzoxazolyl)stilbene compounds(see e. g. col 1, line 5), which corresponds to the second benzoxazole-based optical brightener of claim 5. Wang‘828 teaches reacting 4,4′-stilbenedicarboxylic acid with 2-aminophenol compounds in the presence of a tin or titanium catalyst and an inert organic solvent having a boiling point above 200°C(see e.g. col. 2, line 18, 32). Wang‘828 further teaches that the products are useful as optical brightening or whitening agents and may be obtained by a simple one-step process(see e.g. col. 1, line 43).
Wang‘828 teaches the reaction time and temperature limitations of claims 2 and 3( see e.g. col. 2, line 32, col. 2, line 62). Wang ‘828’s process uses a high-boiling inert solvent, and the example heats the reaction mixture stepwise at 220°C, 230°C, 240°C, 250°C, and 260°C, for about one hour at each temperature, i.e., about five hours total, which falls within the claimed 2–6 hours and 220–270°C ranges.
Ma and Wang‘828 do not teach the use of liquid paraffin in the reaction mixture.
Krull teaches the same field of bisbenzoxazole synthesis(see e.g. cover page, (57), abstract). Krull teaches producing bisbenzoxazoles by reacting o-aminophenols with dicarboxylic acids in the presence of a dehydrating catalyst and solvent(see e.g. p. 7 col. 1, claim 1). Krull expressly identifies thiophene-2,5-dicarboxylic acid and stilbene-4,4′-dicarboxylic acid as suitable dicarboxylic acids(see e.g. p. 2 col. 2, [0021]), and teaches that the process is especially suitable for preparing 4,4′-bis(benzoxazol-2′-yl)stilbene and 2,5-bis(benzoxazol-2′-yl)thiophene(see e.g. p. 4 col. 1, [0031]). Krull also teaches the solvent principle that makes liquid paraffin obvious(see e.g. p. 3 col.2, [0030]). Krull teaches that preferred solvents include aromatic and/or aliphatic hydrocarbons, including decane, pentadecane, decalin, and commercial hydrocarbon mixtures such as petroleum fractions, kerosene, Exxsol, Isopar, and Shellsol. Liquid paraffin is a highly refined paraffinic/naphthenic liquid hydrocarbon mixture, also known as mineral oil or white mineral oil(see e.g. p. 3 col.2, [0030]). Krull further teaches catalyst and nitrogen limitations ( see e.g. p. 3, col. 1, [0022], p. 4, col. 2, [0037]). Krull teaches acidic catalysts including boric acid, phosphoric acid, polyphosphoric acid, zinc chloride, and especially boric acid and titanates such as titanium tetrabutoxide and titanium tetraisopropoxide(see e.g. p. 3, col. 1, [0023]). Krull also teaches that the process may be performed in an inert protective gas such as nitrogen, argon, or helium to prevent side reactions and prepare pure products( see e.g. p. 4, col. 2, [0037]).
Krull does not expressly identify liquid paraffin by name.
Wang‘189 teaches that liquid paraffin was known in organic synthesis as a high-boiling, stable reaction solvent(see e.g. cover page, abstract). Wang ‘189 teaches using liquid paraffin as a reaction solvent, followed by suction filtration, washing, and drying to obtain the product(see e.g. claim page, claims). Wang ‘189 also teaches that liquid paraffin has high boiling point and good stability, can replace another solvent/reactant medium, and helps maintain yield and purity(see e.g. p. 1 [0008]).
Ma, Wang‘828, Krull and Wang‘189 do not expressly state that bisbenzoxazole formation is a dehydration condensation reaction for which liquid paraffin is suitable as ahigh-boiling insert medium.
Kimura et al. teaches the specific relationship between dehydration condensation and liquid paraffin(see e.g. p. 3, [0019-0020]). Kimura et al. teaches dehydration/condensation in a high-boiling inert solvent at 120–320°C(see e.g. p. 3 [0019-0020]), and expressly lists normal paraffin and liquid paraffin among suitable high-boiling inert solvents.
Regarding claim 1, Ma teaches thiophene-2,5-dicarboxylic acid + p-tert-butyl-o-aminophenol + boric acid to make the thiophene bisbenzoxazole product. Wang’828 teaches stilbene-4,4′-dicarboxylic acid + 2-aminophenol + tin/titanium catalyst to make the stilbene bisbenzoxazole product. Krull teaches the same bisbenzoxazole reaction class, hydrocarbon/petroleum solvent media, catalysts, and nitrogen. Wang‘189 and Kimura et al. teach liquid paraffin as a high-boiling inert/reaction solvent useful in organic synthesis and dehydration condensation.
Regarding claim 2, Wang‘828 teaches about five hours total heating, within the claimed 2–6 hours. Krull’s examples also show bisbenzoxazole reaction completion within short reaction times under elevated temperature conditions.
Regarding claim 3, Ma teaches reaction temperature about 230°C; Wang‘828 teaches 220–260°C; Krull examples teach about 220–230°C; all fall within 220–270°C.
Regarding claim 4, Ma teaches 2,5-bis(5-tert-butyl-2-benzoxazolyl)thiophene, corresponding to 2,5-thiophenediylbis(5-tert-butyl-1,3-benzoxazole).
Regarding claim 5, Wang‘828 teaches 4,4′-bis(2-benzoxazolyl)stilbene. Krull also identifies 4,4′-bis(benzoxazol-2′-yl)stilbene as an especially suitable product.
Regarding claim 6, teaches boric acid; Wang ‘828 teaches tin/titanium catalysts; Krull teaches boric acid, phosphoric acid, zinc chloride, titanium tetrabutoxide, and titanium tetraisopropoxide.
It would have been obvious to a person of ordinary skill in the art before the effective filing date to modify the benzoxazole optical-brightener synthesis methods of Ma and Wang‘828 by replacing the prior high-boiling organic solvent system with liquid paraffin as taught by Krull and Wang‘189, Ma and Wang ‘828 teach the claimed thiophene and stilbene bisbenzoxazole products and the corresponding acid/aminophenol condensation chemistry. Krull teaches that the same bisbenzoxazole reaction class may be conducted in hydrocarbon media, including aliphatic hydrocarbons and petroleum hydrocarbon mixtures. Because liquid paraffin is itself a paraffinic/petroleum hydrocarbon medium, one of ordinary skill would have recognized it as a predictable member of the same class of high-boiling hydrocarbon media taught by Krull. The reason to make the substitution is that bisbenzoxazole formation from dicarboxylic acids and aminophenols is a dehydration/condensation reaction requiring a heat-stable reaction medium capable of supporting elevated temperatures and removal or management of generated water. Kimura et al. teaches that liquid paraffin was already known as a high-boiling inert solvent for dehydration condensation at temperatures overlapping the claimed range. Wang‘189 further confirms that liquid paraffin was known as a stable, high-boiling reaction solvent that could be used in organic synthesis and followed by filtration, washing, drying, and recovery of product. The substitution of liquid paraffin for xylene, trichlorobenzene, methylnaphthalene, or NMP would have yielded predictable results because liquid paraffin performs the same expected function as the prior-art hydrocarbon/high-boiling inert solvent: it provides a nonpolar, heat-stable reaction medium or dispersing medium, allows elevated-temperature dehydration condensation, permits suspension/crystallization of the bisbenzoxazole product, and facilitates product recovery by filtration.
Therefore, the claimed invention is prima facie obvious to one of ordinary skill in the art at the time the application was filed, absent factual evidence to the contrary.
Conclusion
No claims are allowed.
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/G.S./Examiner, Art Unit 1628
/AMY L CLARK/Supervisory Patent Examiner, Art Unit 1628
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