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 .
Election/Restrictions
Applicant’s election without traverse of Group I, Claims 1-11 in the reply filed on 27 May 2026 is acknowledged. Claim 12 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected Group II, there being no allowable generic or linking claim. Herein, claims 1-11 are examined on the merits.
Priority
This application is a Continuation of PCT/CN2023/134369 which claims the benefit of CN 202311407946.5 and CN 202211578375.7 with an effective filing date of 09 December 2022 as reflected in the filing receipt mailed on 25 June 2025.
Information Disclosure Statement
The information disclosure statement (IDS) submitted is in compliance with the provisions of 37 CFR 1.97. Accordingly, the information disclosure statement has been considered by the examiner.
Claim Objections
Claim 6 is objected to because of the following informalities:
Claim 6, line 3 states “of mass of the cardanol”, which appears to include a typographical mistake. Herein, claim 6 is interpreted to state “of the mass of the cardanol”.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claims 2-10 are rejected under 35 U.S.C. 112(b) as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor regards as the invention.
The terms “a certain temperature” in claim 2 step (1) and step (3) are relative terms which render the claim indefinite and unclear. The terms “a certain temperature” are not defined in claim 2 and one of ordinary skill in the art would not be reasonably apprised of the scope of the invention recited in claim 2. The term “a certain temperature” in step (1) is defined in claim 4 and the term “a certain temperature” in step (3) is defined in claim 7. For clarity, the specific temperatures should be incorporated into claim 2 instead of the indefinite and unclear terms “a certain temperature”.
Claims 3-9 depend from base claim 2 and are included in this rejection as they do not correct the informalities identified in base claim 2.
Claim 6 recites the limitations “the cardanol to the phenol in step (3)” in line 2 and “mass of the cardanol” in line 3. There is insufficient antecedent basis for these limitations in the claim. Claim 2, step (3) is directed to the “product B with phenol” not to cardanol with phenol. Claim 6 is herein interpreted to state “the product B to the phenol in step (3)” and “mass of the product B”.
Claim 10 recites the limitations “a temperature” in step (2) and in step (4). If the temperature is maintained “at 50°C to 70°C” in step (1) and the same reaction temperature is raised to “75°C” in step (2), the term “a temperature” in step (2) lacks proper antecedent basis. The term “a temperature” in step (2) is interpreted as “the
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.
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.
Claim 1 is rejected under 35 U.S.C. 103 as being unpatentable over Suzuki (US20190010416, published 10 January 2019).
Suzuki is in the known prior art of liquid phenolic resol resin compositions prepared by reacting phenols with aldehydes and catalyst then further reactions of the product bisphenol with phenols, aldehydes, and a catalyst, see Abstract; Paras. [0012]-[0043], where the catalyst is an acid or a base catalyst, see Paras. [0015];[0042];[0049].
Regarding the limitations of instant application claim 1, Suzuki teaches a cardanol-based bisphenol formula P-4,
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, where R1 and R2 “each independently represent a hydrogen atom or —CH2OH”, “R4′ represents a linear unsaturated hydrocarbon group having 10 or more carbon atoms”, “even more preferably a linear unsaturated hydrocarbon group having 12 to 18 carbon atoms”, “* represents a bond” to hydrogen, and the methylene group may be in the ortho position, see Paras. [0023]-[0032];[0040]-[0041], meeting most of Formula (1), where R is C15H31, n is 0, the linking group is methylene, and X1 and X2 are both a hydrogen atom or —CH2OH in instant application claim 1.
Suzuki teaches in formula P-4 the methylene is not specifically attached to a position on either phenol ring and may be attached in the ortho-position of the phenolic hydroxyl on the benzene with the linear unsaturated hydrocarbon group having 12 to 18 carbon atoms, see Paras. [0023]-[0032];[0040]-[0041].
Suzuki does not specifically teach the instant application claim 1 limitations of the methylene is attached in the ortho-position of the phenolic hydroxyl on the benzene with the R group having the linear unsaturated hydrocarbon group with 15 carbon atoms, the methylene is located at an ortho- or para-position of the phenolic hydroxyl on benzene, and the R group has 15 carbon atoms.
Since “[o]bviousness based on structural similarity … can be proved by identification of some motivation that would have led one of ordinary skill in the art to select and then modify a known compound (i.e. a lead compound) in a particular way to achieve the claimed compound” Eisai, 533 F.3d at 1357, 87 USPQ2d at 1455.”, see MPEP 2143 I. B., Example 9, it would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to have modified the lead compound P-4 of Suzuki via positional substitution of the methylene by selecting the methylene is attached in the ortho-position of the phenolic hydroxyl on the benzene with the linear unsaturated hydrocarbon group having 15 carbon atoms and the methylene is attached at the ortho- or the para-position of the phenolic hydroxyl on benzene from the four to five possible choices on the phenol rings for the methylene attachment and the preferred seven possible choices for the number of carbons atoms of Suzuki with a reasonable expectation of success. One of ordinary skill in the art would have been motivated to make these modifications to the lead compound P-4 of Suzuki because Suzuki provides a finite number of identified, predictable solutions, and a person of ordinary skill in the art has good reason to pursue the known options within his or her technical grasp, such as the attachment of the methylene bridge and the number of carbon atoms in the linear unsaturated hydrocarbon group for the benefit of efficiently obtaining “a liquid phenolic resol resin which is excellent in view of curing properties as characteristics of a phenolic resin and suitable for obtaining a wet-type paper friction material having excellent flexibility and durability”, see Suzuki, Paras. [0023]-[0032]; and, MPEP 2144.05 IIB.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
Claims 2-9 are rejected under 35 U.S.C. 103 as being unpatentable over Kong et al. (CN103012743, published 03 April 2013, see machine translation, hereinafter Kong) in view of Suzuki (US20190010416, published 10 January 2019) in further view of Koyama et al. (WO2022145280, published 07 July 2022, hereinafter Koyama, WO2022145280 is translated as US20240010798 which is serving as the English language equivalent and all citations in this action pertain to this US reference).
Kong is in the known prior art field of “a cashew novolac epoxy resin and a preparation method thereof” by “reacting anacardol with formaldehyde under the effect of a catalyst, so as to obtain reddish-brown liquid cashew novolac resin; reacting the cashew novolac resin with epichlorohydrin for 4 hours at 80 to 120 DEG C under the catalyzing effect of quaternary ammonium salt; cooling the reactant to reach 70 DEG C; respectively adding alkali at 8 to 12 times within 2 hours; reacting for 1 to 6 hours at 70 to 90 DEG C; washing with hot water until appearing neutral; standing to stratify; removing the water layer; and reducing the pressure and distilling to remove excessive epichlorohydrin, so as to obtain the reddish-brown liquid novolac epoxy resin”, see Abstract, where the reaction takes place with an acidic or a basic catalyst at temperatures of “70-100℃ for 2-4 hours”, see Paras. [0012];[0015];[0036].
Regarding the limitations of instant application claims 2, 4, and 5, Kong teaches a method of preparing a “cashew phenolic epoxy resin” by “reacting cashew phenol with formaldehyde at 70-100℃ for 2-4 hours under the action of a catalyst”, see Paras. [0012];[0035]-[0036], where the cashew phenol molecular
structure “contains the following four types:
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”, i.e., the cashew phenol is cardanol, to prepare “the cashew phenolic epoxy resin”
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see Original, Paras. [0025]-[0029], Machine Translation, Paras. [0030]-[0034], the catalyst is barium hydroxide, see Paras. [0015];[0036], and the reaction takes place in a “flask equipped with a thermometer, stirrer, and condenser”, see Para. [0041], meeting:
Step (1) in instant application claim 2;
Within the time and temperature ranges in instant application claim 4;
The specific catalysts, barium hydroxide, in instant application claim 5;
The reaction product “is then washed with water, allowed to stand and separate into layers, the water layer is removed, and the remaining water is removed by vacuum distillation to obtain a brownish-red liquid cashew phenol aldehyde resin”, see Paras. [0012];[0036], where the water washing is “until neutral”, see Para. [0014], meeting:
Step (2) washing with water and removing water to obtain a product in instant application claim 2;
After a step, the products produced in the steps is washed “until neutral”, allowed “to stand and separate into layers”, the aqueous layer is removed, and excess material is removed “by vacuum distillation to obtain a brownish-red liquid cashew phenolic epoxy resin”, see Paras. [0014];[0038], meeting:
Step (4) in instant application claim 2; and,
The method for preparing cardanol-based phenol in instant application claim 2.
Regarding the limitations of instant application claim 3, Kong teaches “the amount of catalyst used is 1%-3% of the mass of cashew phenol, and the amount of formaldehyde used is 0.5-1.0 times the mass of cashew phenol”, see Paras. [0012];[0036], i.e. mass ratio of cardanol to catalyst of 100:1 to 100:3 or 1:0.01 to 1:0.3, meeting:
Within the molar ratio and mass ratio in instant application claim 3.
Kong does not teach:
The instant application claim 2 limitations of a method for preparing cardanol-based bisphenol, comprising the following steps: (2) washing the product A multiple times, and then centrifuging to remove water; (3) mixing and uniformly stirring the product B with phenol and an acidic catalyst, and reacting at a certain temperature to obtain a product C after a phenolic alcohol reaction; and (4) obtaining a cardanol-based bisphenol; and,
The limitations of instant application claims 6-9.
Suzuki is in the known prior art of liquid phenolic resol resin compositions prepared by reacting phenols with aldehydes and catalyst then further reactions of the product bisphenol with phenols, aldehydes, and a catalyst, see Abstract; Paras. [0012]-[0043], where the catalyst is an acid or a base catalyst, see Paras. [0015];[0042];[0049], and is applied to teach the same.
Regarding the limitations of instant application claims 2, 7, and 8, Suzuki teaches reacting phenols, such as “at least one or more phenols selected from the group consisting of cardanol, cardol, and 2-methyl cardol”, with “an acid catalyst”, such as “such as acetic acid or oxalic acid, a mineral acid such as hydrochloric acid, sulfuric acid, or phosphoric acid, diethyl sulfate, p-toluenesulfonic acid, p-phenolsulfonic acid, and the like” to obtain a bisphenol product, see Paras. [0015]-[0018];[0036]-[0044], where the reaction includes “a reaction apparatus including a stilling device, a reflux condenser, and a thermometer, heated to 140° C., and reacted for 1 hour with stirring”, and the reaction product is neutralized, see Para. [0061], or “a reaction apparatus including a stirring device, a reflux condenser, and a thermometer, heated to 60° C. and reacted for 30 minutes with stirring”, see Para. [0070], meeting:
Step (3) mixing phenols and an acidic catalyst and reacting to obtain a product in instant application claim 2;
Within the temperature and time range in instant application claim 7; and,
The specific acids in instant application claim 8.
Koyama is in the known prior art field of compounds of formula (1) conventionally obtained from the reaction of “lignin, phenol or a phenol derivative, and aldehydes” “with a novolac-type phenol resin in the presence of an organic acid” and treatment “with volatile organic bases, etc.”, such as “an organosolv method, a pressurized hydrothermal method, a steam explosion method, an ammonia treatment method, an ammonia explosion method, an acid treatment method, a dilute sulfate explosion method, an alkali treatment method, an oxidative decomposition method, a pyrolysis method and a microwave heating method”, see Abstract; Paras. [0002]-[0005];[0076]. The compound of formula (1) is a cardanol-based bisphenol represented by:
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, where “Ra is a hydrogen atom”, “Rc1 and Rc2 are independently a hydroxyl group”, R11 and R13-R20 “are independently a hydrogen atom”, and R12 is “a hydrocarbon group including 1 to 15 carbon atoms”, see Paras. [0017]-[0029];[0052];[0073]-[0076];[0089], and is applied to teach the same.
Regarding the limitations of instant application claims 2 and 9, Koyama teaches a method for preparing cardanol-based bisphenol, see Paras. [0017]-[0029];[0052];[0073]-[0076];[0089], where the obtained reaction step products are “diluted and/or washed with a solvent and filtered”, the dilution solvent and washing solvent is water, i.e., multiple washes with water, “the solid-liquid separation is not particularly limited, and for example, a filtration apparatus using filter or the like, a vacuum filter, a centrifugal separator, a screw decanter, dehydrators such as a belt press dehydrator, a screw press dehydrator, and a filter press dehydrator, a vibrating sieve, or the like”, and “a solid-liquid separation step may be subjected to distillation. The distillation may be performed by vacuum distillation at the temperature of about 40 to 200° C., usually about 50 to 150° C., and under reduced pressure of about 3 to 20 kPa, usually about 5 to 10 kPa to remove the solvent”, i.e., 0.003 to 0.02 MPa, see Paras. [0113]-[0118], meeting:
The cardanol-based bisphenol product in instant application claim 2;
The step (2) water washings and centrifuging in instant application claim 2; and,
Within the distillation temperature in instant application claim 9.
Kong and Koyama do not specifically teach the distillation time and pressure range limitations in instant application claim 9.
Regarding the time and pressure range limitations of instant application claim 9, Kong teaches removing excess reactants “by vacuum distillation to obtain a brownish-red liquid cashew phenol aldehyde resin”, see Paras. [0012];[0014];[0036];[0038].
Koyama teaches in order to obtain the product “as a solid or viscous solid” “filtration, distillation, and decompression to dryness may be performed alone or in combination of two or more thereof”, see Paras. [0117]-[0124];[0163], the filtering is “under about 0.1 to 0.99 MPa, usually about 0.1 to 0.4 MPa”, and the “extraction pressure may be set as appropriate, for example, 0.1 MPa or higher, or 0.5 MPa or higher, or 1.0 MPa or higher, and 10 MPa or lower, 5 MPa or lower, 4 MPa or lower, or 3 MPa or lower”, see Paras. [0111]-[0113].
In reference to the time and pressure range in instant application claim 9, since “a prima facie case of obviousness exists” where the claimed ranges “overlap or lie inside ranges disclosed by the prior art”, and where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05. Both Kong and Koyama teach vacuum distillation and purification pressure ranges within the claimed range to removed excess reactants and to isolate the product; therefore, “the general conditions of [the] claim are disclosed in the prior art, [and] it is not inventive to discover the optimum or workable ranges by routine experimentation”, see MPEP 2144.05. It would have been obvious to one of ordinary skill in the art, before the effective filing date of the claimed invention, to predictably modify the distillation time and pressure of Kong to determine the time frame for distillation in order to isolate the desired product as a solid or viscous solid, see Koyama, Paras. [0117]-[0124];[0163], meeting:
Within the distillation time and pressure range in instant application claim 9.
Kong and Suzuki do not specifically teach the limitations of instant application claim 6.
Regarding the limitations of instant application claim 6, Koyama teaches “the organic solvent A may be used alone or in combination of two or more thereof”, where “10% by mass or more, 20% by mass or more, 30% by mass or more, 40% by mass or more, 50% by mass or more, 60% by mass or more, 70% by mass or more, 80% by mass or more, 90% by mass or more, 95% by mass or more, 97% by mass or more, or 99% by mass or more of the organic solvent is the organic solvent A”, see Paras. [0094]-[0096], “the organic solvent A, for example, one or two or more selected from compounds represented by the formula (II)”, such as phenol, see Paras. [0092]-[0093], “the organic solvent A typically contains at least a compound represented by the formula (I)”, such as cardanol, see Paras. [0074];[0089], for example, the organic solvent contains 50% by mass cardinal and 50% by mass phenol, i.e., a 1:1 ratio, and the “amount of the acid catalyst may be, for example, larger than 0% by mass, 0.1% by mass or more, or 0.2% by mass or more, and may be 5.0% by mass or less, 3.0% by mass or less, or 2.6% by mass or less, where the total amount of lignin and the solvent is 100 parts by mass”, see Paras. [0105]-[0107], for example, 50 parts by mass cardanol with as calculated by the examiner 0.1% mass acid catalysts/2 is 0.05 mass of catalyst of the mass of the cardanol, meeting:
Within the step (3) molar ratio and amount mass in instant application claim 6.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified the cardanol-based phenol preparation method of Kong to incorporate the cardanol-based phenol preparation washing of the product and removal of reactants and by products, along with further reacting the product to obtain an additional product at the optimal concentration of reactants, temperatures, times, and pressures, as taught by Suzuki and Koyama with a reasonable predictability of success for the purpose of efficiently producing a cardanol-based phenol “which is excellent in view of curing properties as characteristics of a phenolic resin” “having excellent flexibility and durability”, see Suzuki, Paras. [0023]-[0032]; Koyama, Paras. [0002]-[0005];[0012].
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying the cardanol-based phenol preparation method of Kong by applying the known technique of the cardanol-based phenol preparation washing of the product and removal of reactants and by products, along with further reacting the product to obtain an additional product at the optimal concentration of reactants, temperatures, times, and pressures, as taught by Suzuki and Koyama with a reasonable predictability of success for the purpose of efficiently producing a cardanol-based phenol “which is excellent in view of curing properties as characteristics of a phenolic resin” “having excellent flexibility and durability”, see Suzuki, Paras. [0023]-[0032]; Koyama, Paras. [0002]-[0005];[0012]; and MPEP 2143 I. B-D.
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”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Kong, Suzuki, and Koyama all teach cardanol-based phenol preparation methods, a person of ordinary skill in the art has good reason to modify Kong by relying upon Suzuki and Koyama before the effective filing date of the claimed invention for knowledge generally available within the cardanol-based phenol preparation art regarding the washing of the product and removal of reactants and by products, along with further reacting the product to obtain an additional product at the optimal concentration of reactants, temperatures, times, and pressures, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a cardanol-based phenol “which is excellent in view of curing properties as characteristics of a phenolic resin” “having excellent flexibility and durability”, see Suzuki, Paras. [0023]-[0032]; Koyama, Paras. [0002]-[0005];[0012]; and, MPEP 2141 and 2143 I. B-D.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
“The normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the concentration of reactants, temperatures, times, and pressures, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Selection of a known material, such as an acid or a base catalyst, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as the concentration of reactants, times, and pressures, “or degree,” such as temperatures, “or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Claims 10 and 11 are rejected under 35 U.S.C. 103 as being unpatentable over Suzuki (US20190010416, published 10 January 2019), as applied in the 35 USC 103 rejection of claim 1 above, in view of Tian et al. (CN1374299, published 16 October 2002, see machine translation, hereinafter Tian) and in further view of Kai et al. (CN114316242, published 12 April 2022, see machine translation, hereinafter Kai) and Hassanpour, (“A Review of Four Kinds of Resin Production Technologies Based On Recent Developments”, May-Aug 2021, SSRG International Journal of Industrial Engineering, Vol. 8, Iss. 2, Pgs. 1-12), as evidenced by Shirtum et al. (EP0363857, published 18 April 1990).
Regarding the limitations of instant application claim 10, Suzuki teaches using the cardanol-based bisphenol “liquid phenolic resol resin” of formula P-4 as raw material in the synthesis of an impregnated paper, by mixing the cardanol-based bisphenol in a acetone composition, see Paras. [0011];[0029]-[0032];[0074]-[0076], and “[o]wing to its excellent mechanical characteristics, electric characteristics, and adhesiveness, the phenolic resin is used in various fields”, see Paras. [0003]-[0004], meeting:
The using the cardanol-based bisphenol according to claim 1 as raw material, the method comprises the following steps: (1) stirring the cardanol-based bisphenol in instant application claim 10.
Suzuki does not teach the remainder of the limitations in instant application claim 10.
Tian is in the known prior art field of “the synthesis of cardanol glycidyl ether” by reacting cashew “shell oil and chloropropylene oxide” “in the presence of sodium hydroxide”, with the “cashew nut shell oil: epichlorohydrin: sodium hydroxide molar ratio used in this invention is 0.8-1.1: 1.5-3.0: 0.8-2.0”, where the cardanol glycidyl ether “has in its molecular structure epoxy radical, phenyl radical and long-chain substituted radical, has high electrochemical corrosion resistance and high water resistance and can may be used in long-term wet corrosive environment”, see Abstract; Paras. [0004]-[0005]; and, the below Scheme, and is applied to teach the same.
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Regarding the limitations of instant application claim 10, Tian teaches a method for preparing a cardanol phenol based epoxy resin, see Abstract and the above Scheme, by mixing in step 1, cashew nut shell oil aka cardanol and epichlorohydrin aka epoxy chloropropane in a nitrogen environment with “a 30% sodium hydroxide solution” added dropwise while “controlling the temperature at 50-55℃ for 3-4 hours”, see Paras. [0006]-[0015];[0019], meeting:
The step (1) stirring the cardanol phenol and epoxy chloropropane within the temperature range in the presence of a nitrogen catalyst, then adding NaOH solution and maintaining a constant temperature in instant application claim 10;
In step 2, the temperature is raised “to 70-75℃” and the reaction is kept warm “for 3-4 hours” then the “temperature was raised to 80±2℃, and excess epichlorohydrin and water were recovered under reduced pressure at a vacuum level of 160 mmHg” “until no distillate is obtained”, where “[a]fter centrifuging and filtering the product, the first batch of products was obtained”, then “[t]he filter residue was extracted with toluene, filtered, and the toluene was distilled off to obtain the second batch of product”, see Paras. [0012];[0020]-[0023]; Claim 1, meeting:
The step (2) within the raising the temperature range, maintaining water separation, and performing distilling under reduced pressure to remove the epoxy chloropropane in instant application claim 10;
The step (3) filtering or centrifuging in instant application claim 10;
The step (4) obtaining a filtrate, further distilling, and obtaining a cardanol phenol based epoxy resin in instant application claim 10; and,
The method of preparing a cardanol phenol based epoxy resin in instant application claim 10.
Regarding the limitations of instant application claim 11 of “[t]he cardanol phenol based epoxy resin, prepared by the preparation method according to claim 10”, see MPEP 2113(I) stating “even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process.” In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985) (citations omitted)”. Tian teaches the cardanol phenol based epoxy resin made by substantially the same process as instant claim 10; therefore, the process of production is not given patentable weight, meeting the limitations in instant application claim 11.
Suzuki and Tian do not teach:
The instant application claim 10 limitations of (1) stirring the raw materials for 5 min to 15 min in the presence of a quaternary ammonium salt catalyst, maintaining a constant temperature for 40 min to 90 min; (2) further adding a NaOH solution, testing a recovered water amount, stopping a reaction after the recovered water amount reaches a theoretical amount; (3) filtering or centrifuging to remove a salt; and (4) raising a temperature to 110°C, further performing distilling under reduced pressure to remove the epoxy chloropropane.
Regarding the instant application claim 10 step (4) limitations of raising a temperature to 110°C, further performing distilling under reduced pressure to remove the epoxy chloropropane. Tian teaches “excess epichlorohydrin and water were recovered under reduced pressure at a vacuum level of 160 mmHg” aka 21.33 kPa “until no distillate is obtained”, see Paras. [0012];[0020]-[0023]; Claim 1. As evidenced by Shirtum et al., the boiling point of epichlorohydrin is based on the reaction pressure and at vacuum pressures of “6.895 kPa (1 psia) to 6895 kPa (1000 psia)” and “temperatures above 100°C” “epichlorohydrin is boiled out”, see Pg. 5, Ln. 21-Pg. 6, Ln. 1. Therefore, it is inherent depending on the pressure that the vacuum distillation of Tian is performed at a temperature within the range of 110°C that will evaporate all of the epichlorohydrin and water, see MPEP 2112. In addition, “a prima facie case of obviousness exists” where the claimed ranges or amounts do not overlap with the prior art but are merely close, see MPEP 2144.05, and duplication of method steps, such as the vacuum distillation of Tian is also obvious to one or ordinary skill in the art, see MPEP 2144.04. As a result, it would have been obvious to one or ordinary skill in the art, before the effective filing date of the claimed invention, to predictably determine the vacuum distillation temperature of around 110°C to evaporate all of the epichlorohydrin and water and to the repeat the process in order to boil out all of the epichlorohydrin, meeting:
Within the step (4) vacuum distillation temperature range in instant application claim 10; and,
The step (4) duplication of performing distilling under reduced pressure to remove the epoxy chloropropane in instant application claim 10.
Kai is in the known prior art field of “a cardanol-based Gemini anion-nonionic surfactant as well as a preparation method and application of the cardanol-based Gemini anion-nonionic surfactant”, see Abstract, and is applied to teach the same.
Regarding the limitations of instant application claim 10, Kai teaches “(i) Cashew phenol is reacted with an epoxy compound under the action of a catalyst to obtain cashew phenol polyoxyethylene ether”, see Paras. [n0017]-[n0018], where the epoxy compound is epichlorohydrin, see Para. [n0021], the catalyst is “triethylamine, benzyltriethylammonium chloride, tetrabutylammonium bromide and tetrabutylammonium hydrogen sulfate”, see Para. [n0022], “the reaction temperature is 40-120 ◦C; preferably, the reaction temperature is 60-100 ◦C”, and “the residence time of the reaction is 5-35 min; preferably, the residence time of the reaction is 15-25 min; more preferably, the residence time of the reaction is 20 min”, see Paras. [n0026]-[n0027], “the reaction is carried out in a microchannel reactor; preferably, the mixture of cashew phenol and catalyst, and the epoxide compound are simultaneously pumped into the microchannel reactor for reaction”, see Para. [n0024], meeting:
Step (1) stirring the raw materials for 5 min to 15 min in the presence of a quaternary ammonium salt catalyst in instant application claim 10;
The reaction solution is neutralized by sodium hydroxide, where “preferably, after the reaction is completed, excess 5 mol/L sodium hydroxide is added for neutralization, and after stirring for 1 hour”, see Para. [n0055], and the reaction solution is “filtered to remove inorganic salts, and the solvent was evaporated from the filtrate at 50 ◦C and 133Pa pressure”, see Para. [n0121] meeting:
Step (2) further adding a NaOH solution in instant application claim 10; and,
Step (3) filtering to remove a salt in instant application claim 10.
Hassanpour is in the known prior art field of “Bakelite, Alkyd, Epoxy resins, and Urea-Formaldehyde (UF) adhesive production technologies”, see Abstract, where “[b]akelite or phenol-formaldehyde resin is produced from the reaction between phenol and formaldehyde and has two types of Novolak resin and Russell resin. If the molar ratio of formaldehyde to phenol is less than one and an acid catalyst is used, Novolak resin is synthesized, which this process is fulfilled in two stages of curing or networking. If the molar ratio of formaldehyde to phenol is more than one and a base catalyst is exploited, Russell resin is processed, which is converted into a polymer network in one step”, see Pgs. 6-7, C. Bakelite resin; Pg. 9, IV. Bio-bases epoxy resins, and is applied to teach the same.
Regarding the limitations of instant application claim 10, Hassanpour teaches “EpiChloroHydrin(ECH)” “and bisphenol A are introduced into the reactor to produce epoxy resin”, where in “the second stage of the reaction, in the presence of sodium hydroxide, the chlorohydrin ether mediates the production of the epoxy radical … To complete the polymerization process, the resulting polymer is separated from the polymer by a storage tank in which the polymer is evaporated under a vacuum chamber of 5 mm Hg. The polymer whose ECH has been removed resumes reacting with unreacted by-products and raw materials. To remove the reaction by-products and complete the reaction of unreacted materials, the next step is accomplished via purification reactions, in which sodium hydroxide is added to repeat the reaction, which removes a large number of chlorine compounds”, see Pgs. 3-4, A. The epoxy resin industries, further meeting:
The step (1) reactants and the step (2) further adding a NaOH solution in instant application claim 10;
The removal of water from the system is controlled by temperature, “by vacuum pump and creating a relative vacuum of about 30 mm Hg by distillation and reflux. It results to distill and dehydration. The surplus water is separated from the resin. Due to the higher concentration of the product, the liquid water vapor is collected in the condenser in a special container. If the resin is a liquid product, distillation is done for a shorter time, and when its solid percentage comes into view(60-70%) is emptied into the filter and then is sent to a storage tank to be packed in barrelsof200 kg. If the production of solid resin is the goal, the distillation operation is performed until complete dewatering, and the molten resin is cooled to near the melting point of about 50 °C. … In all the above cases, after a laboratory check-up to complete the reaction and create the desired product, the produced resin is washed with a dilute sulfuric acid solution, and its pH is neutralized.”, see Pgs. 6-7, C. Bakelite resin, meeting:
The step (2) testing a recovered water amount and stopping a reaction after the recovered water amount reaches a theoretical amount in instant application claim 10.
Regarding the instant application claim 10 step (2) limitation of maintaining a constant temperature for 40 min to 90 min. Kai teaches “the residence time of the reaction is 5-35 min; preferably, the residence time of the reaction is 15-25 min; more preferably, the residence time of the reaction is 20 min”, see Paras. [n0026]-[n0027], and Hassanpour teaches “sodium hydroxide is added to repeat the reaction, which removes a large number of chlorine compounds”, see Pgs. 3-4, A. The epoxy resin industries. Therefore, the reaction time detailed in Kai is doubled to 10 to 70 minutes, meeting within the step (2) reaction time in instant application claim 10.
In reference to the above claims, it would have been obvious to one of ordinary
skill in the art, before the effective filing date of the claimed invention, to have modified Suzuki to use the cardanol-based phenol resin to prepare a cardanol-based phenol epoxy resin, as taught by Tian, Kai, and Hassanpour with a reasonable predictability of success for the purpose of efficiently producing a bio-based epoxy resin having a “molecular structure epoxy radical, phenyl radical and long-chain substituted
radical” with “high electrochemical corrosion resistance and high water resistance” that “can may be used in long-term wet corrosive environment”, see Tian, see Abstract; Paras. [0004]-[0005]; Kai, Paras. [n0003];[n0007]; Hassanpour, Pgs. 6-7, C. Bakelite resin; Pg. 9, IV. Bio-bases epoxy resins.
A rationale to support a conclusion that the claim would have been obvious is that a particular known technique was recognized as part of the ordinary capabilities of one skilled in the art. Another rationale to support a conclusion that the claim would have been obvious is that the substitution of one known element for another yields predictable results to one of ordinary skill in the art. One of ordinary skill in the art would have been capable of modifying Suzuki to use the cardanol-based phenol resin by applying the known technique of preparing a cardanol-based phenol epoxy resin, as taught by Tian, Kai, and Hassanpour with a reasonable predictability of success for the purpose of efficiently producing a bio-based epoxy resin having a “molecular structure epoxy radical, phenyl radical and long-chain substituted radical” with “high electrochemical corrosion resistance and high water resistance” that “can may be used in long-term wet corrosive environment”, see Tian, see Abstract; Paras. [0004]-[0005]; Kai, Paras. [n003];[n0007]; Hassanpour, Pgs. 6-7, C. Bakelite resin; Pg. 9, IV. Bio-bases epoxy resins; and MPEP 2143 I. B-D.
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”, see MPEP 2143 I.E. Since patents are part of the literature of the prior art relevant for all they contain, see MPEP 2123, and Suzuki, Tian, Kai, and Hassanpour all teach cardanol-based phenol preparation methods, a person of ordinary skill in the art has good reason to modify Suzuki by relying upon Tian, Kai, and Hassanpour before the effective filing date of the claimed invention for knowledge generally available within the cardanol-based phenol preparation art regarding the epoxification of the cardanol-based phenol, see MPEP 2143 B & G and 2141, for the benefit of efficiently producing a bio-based epoxy resin having a “molecular structure epoxy radical, phenyl radical and long-chain substituted radical” with “high electrochemical corrosion resistance and high water resistance” that “can may be used in long-term wet corrosive environment”, see Tian, see Abstract; Paras. [0004]-[0005]; Kai, Paras. [n003];[n0007]; Hassanpour, Pgs. 6-7, C. Bakelite resin; Pg. 9, IV. Bio-bases epoxy resins; and, MPEP 2141 and 2143 I. B-D.
As stated in Sakraida v. Ag Pro, Inc., 425 U.S. 273, 189 USPQ 449, reh’g denied,
426 U.S. 955 (1976), “[w]hen a work is available in one field of endeavor, design
incentives and other market forces can prompt variations of it, either in the same field
or a different one. If a person of ordinary skill can implement a predictable variation, §
103 likely bars its patentability. For the same reason, if a technique has been used to
improve one device, and a person of ordinary skill in the art would recognize that it
would improve similar devices in the same way, using the technique is obvious unless its
actual application is beyond his or her skill”, see MPEP 2141.
“The normal desire of scientists or artisans to improve upon what is
already generally known provides the motivation to determine where in a disclosed set
of percentage ranges”, such as the concentration of reactants, temperatures, times, and pressures, “is the optimum combination of percentages.” In re Hoeschele, 406 F.2d 1403, 160 USPQ 809 (CCPA 1969), see MPEP 2144.05.
Selection of a known material, such as an quaternary ammonium salt catalyst instead of nitrogen gas, based on its suitability for its intended use supported a prima facie obviousness determination in Sinclair & Carroll Co. v. Interchemical Corp., 325 U.S. 327, 65 USPQ 297 (1945), see MPEP 2144.07.
In addition, “[i]t is a settled principle of law that a mere carrying forward of an original patented conception involving only change of form, proportions,” such as the concentration of reactants, times, and pressures, “or degree,” such as temperatures, “or the substitution of equivalents doing the same thing as the original invention, by substantially the same means, is not such an invention as will sustain a patent, even though the changes of the kind may produce better results than prior inventions. In re Williams, 36 F.2d 436, 438, 4 USPQ 237 (CCPA 1929)”, see MPEP 2144.05.
Conclusion
No claims are allowed.
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/YO/Examiner, Art Unit 1692
/FEREYDOUN G SAJJADI/Supervisory Patent Examiner, Art Unit 1699
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