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 .
Claim Interpretation
“Natural aldehyde” is defined in the instant application as an aldehyde, aldehyde compound, or aldehyde component is derived from a renewable source such as a plant and “synthetic aldehyde” is defined in the instant application as an aldehyde, aldehyde compound, or aldehyde component is derived from a nonrenewable source, such as a fossil fuel (pg. 5, [0021-0022]).
Compounds such as formaldehyde, paraformaldehyde, and the like are structurally identical to products produced from natural or synthetic sources. FeedstocksUnited (2024) demonstrates that formaldehyde can be made from methanol oxidation/combustion, with paraformaldehyde being a polymerized version of formaldehyde. FeedstocksUnited goes on to state that methanol can come from renewable sources as well, including sources such as sustainable biomass. While recitation of all aldehydes would be exhaustive, it falls under the broadest reasonable interpretation that aldehydes and derivatives that can be obtained from either synthetic or natural sources and that the modifiers of “natural” and “synthetic” impart product-by process limitations.
Product-by-process claims are not limited to the manipulations of the recited steps, only to the structure implied by the steps. If the product in a product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the product was made by a different process. For more information, see MPEP § 2111 & 2113(I).
Claim Rejections - 35 USC § 102
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (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 the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
(a)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claim(s) 1 – 12 is/are rejected under 35 U.S.C. 102(a)(1) and 102(a)(2) as being anticipated by Banach et al. (US Pub. No. 20150112023 A1), hereafter referred to as Banach.
Regarding claims 1 and 2, Banach teaches the reaction of an alkylphenol compound with an aldehyde, such aldehydes comprising one or more of formaldehyde, paraformaldehyde, furfural, and mixtures thereof (pgs. 1, 4, [0006, 0032]).
Regarding Claims 3 and 4, Banach teaches the reaction discussed in (8) with one or more aldehydes, and mixtures thereof and further teaches that additional aldehyde may be added to react later to adjust the melt point of the resin (pg. 4, [0032, 0034]). Banach goes on to teach a metered addition of formaldehyde in the formation of the alkylphenol-aldehyde resin in 3 distinct stages. Banach adds formaldehyde to the already prepared alkylphenol solution in 3 stages, first in a slow subsurface addition until an exotherm was established, then further added in greater amounts (5/6 of total aldehyde) until formaldehyde addition was completed and lastly added to adjust the melt point (pg. 8, [0076 – 0077]).
As discussed above in (2 – 4), formaldehyde is structurally identical whether synthetically or naturally derived and so meets the structural limitations of both the natural aldehyde of claim 1 and the synthetic aldehyde of claim 3. Consequentially, the use of formaldehyde as the initially added aldehyde and then used again as a later added aldehyde would read on claims 3 and 4. Additionally, given Banach teaches mixtures of the aldehydes mentioned, including formaldehyde, paraformaldehyde, and furfural, an embodiment where formaldehyde is added initially and then furfural is added afterwards would be consistent with Banach’s teachings and would read on claim 4 (pg. 4, [0032, 0034]).
Regarding claims 5 – 6, Banach teaches the method to make an alkylphenol-aldehyde resin as discussed in (8 – 10), where the aldehyde or combination of aldehydes can be added one or more times to the reaction with the alkylphenol, especially to adjust the melt point of the resin.
Banach further teaches the metered addition of formaldehyde in the formation of the alkylphenol-aldehyde resin in 3 distinct stages. Banach adds formaldehyde to the already prepared alkylphenol solution in 3 stages, first in a slow subsurface addition until an exotherm was established, then further added in greater amounts (5/6 of total aldehyde) until formaldehyde addition was completed and lastly added to adjust the melt point (pg. 8, [0076 – 0077]).
As discussed above in (2 – 4, 10), formaldehyde is structurally identical whether synthetically or naturally derived and so meets the structural limitations of both the natural aldehyde of claim 1 and the synthetic aldehyde of claim 3. So, Banach’s first addition is reaction of alkylphenol with a first amount of product structurally identical to the claimed synthetic aldehyde; the second addition is reaction of a product structurally identical to the claimed natural aldehyde; and the third addition is reaction with a second amount of a product structurally identical to the claimed synthetic aldehyde. Banach’s reaction scheme thus reads on claims 5 and 6 with a second synthetic amount of synthetic aldehyde reacted after the natural aldehyde-alkylphenol reaction.
Regarding claim 7, Banach teaches the method of making an alkylphenol resin discussed in (8 – 10), including the reaction of an alkylphenol compound with an aldehyde, such aldehydes comprising one or more of formaldehyde, paraformaldehyde, furfural, and mixtures thereof (pgs. 1, 4, [0006, 0032]). Banach additionally teaches modification of the resin with one or more bases including amines, which are further reacted with the addition of an epoxide to the alkylphenol-aldehyde to stabilize the basic moieties resulting from a reaction in basic conditions (pgs. 4 – 5, [0038 – 0043]). Under basic conditions such as in Banach, epoxides are ring opened by the basic moieties like amines and then react as alkoxides.
Regarding claims 8 – 11, the reasoning discussed in (8 – 10) reads on the claims. Briefly, Banach teaches the alkylphenol-aldehyde resin comprised of furfural, alkylphenol, and optionally (“one or more”) another aldehyde such as formaldehyde (pgs. 1, 4, [0006, 0032, 0034]).
Regarding claim 12, Banach teaches the method to make the alkylphenol-aldehyde resin discussed in (8 – 10, 15), where exemplary alkylphenols include para-methylphenol, para-tert-butylphenol (PTBP), para-sec-butylphenol, para-tert-hexylphenol, para-cyclohexylphenol, para-tert-octylphenol (PTOP), para-isooctylphenol, para-decylphenol, para-dodecylphenol, para-tetradecyl phenol, para-octadecylphenol, para-nonylphenol, para-pentadecylphenol, and para-cetylphenol (pg. 2, [0016]).
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(s) 13 is/are rejected under 35 U.S.C. 103 as being unpatentable over Banach as applied to claims 8 above, and in view of Braden et al. (US Pub. No. 20190202962 A1), hereafter referred to as Braden.
Regarding claim 13, Banach teaches a method of making an (alkyloxy)phenol-aldehyde resin discussed in (8 – 10, 15). Briefly, Banach teaches the alkylphenol-aldehyde resin comprised of furfural, alkylphenol, and optionally (“one or more”) another aldehyde such as formaldehyde (pgs. 1, 4, [0006, 0032, 0034]). Banach teaches the alkylphenol : aldehyde ratio can range from 0.5:1 to 1:0.1 (pg. 4, [0033]).
Braden teaches a method of making an (alkyloxy)alkylphenol-aldehyde resin that is alkoxylated further after (alkyloxy)phenol and aldehyde reaction (pg. 1, [0002]). Braden teaches that ethoxylated alkylphenol/formaldehyde resins have been in the industry as typical chemical demulsifiers (pg. 1, [0006]). Braden formulates the phenolic resin using a 1 : 1 ratio of aldehyde to phenol (pg. 5, [0065]).
It would have been prima facie obvious to one of ordinary skill in the art to use the ratio taught in Braden as a demulsifier embodiment within the ratio range afforded to the resin making method described in Banach, using a ratio recognized by the prior art as being suitable for combining monomers functionally identical to those in Braden to obtain a structurally similar polymer for a similar end use. For more information, see MPEP § 2144.05(I).
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure.
Gupta and Kumar (Reaction Engineering of Step Growth Polymerization, Ch. 11 Plenum Press 1987) teach formaldehyde polymerization and uses.
Cheng and Sui (Iran Polym J 31, 619–628 (2022)) teach glucose-furfural phenolic resin.
Tort et al. (US Pat No. US 12384957 B2) teaches a modified alkylphenol resin and use of the resin for extraction of crude oil.
Gul et al. (US Pub No. 20200102513 A1) teaches processes for making alkoxylated 4-(alkyloxy)phenol/aldehyde resins and demulsifying oil and water.
Vanormelingen et al. (US Pub. No. 20190023829 A1) teaches a process for the preparation of a novolac alkylphenol resin using a defined mixture of mono- and dialkylphenols, an aldehyde, and an acid catalyst.
Banach et al (US Pub. No 20150112024 A1) teaches a process including base-modified alkylphenol-aldehyde resin with a salicylic acid to stabilize the base-modified alkylphenol-aldehyde resin.
Buriks et al. (US Pat. No. US 4098717 A) teaches processes to prepare oxyalkylated pheno-aldehyde resins.
De Groote and Kwan-ting (US Pat. No. 2888403 A) teaches the making of an oxyalkylated phenolic resin modified by a lactone.
IARC (IARC Monographs on the Evaluation of Carcinogenic Risks to Humans Volume 88 (2006): Formaldehyde, 2-Butoxyethanol and 1-tert-Butoxypropan-2-ol, pg. 439 included in Office action) teaches the carcinogenic effect of formaldehyde.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ARMAN M. FARAZDAGHI whose telephone number is (571)270-5813. The examiner can normally be reached Monday - Friday, Monday - Thursday, 8:30 am - 5:00 pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Robert Jones can be reached at (571) 270-7733. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/ARMAN M. FARAZDAGHI/Examiner, Art Unit 1762
/ROBERT S JONES JR/Supervisory Patent Examiner, Art Unit 1762
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