DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA .
Claim Status
Claims 1-4, and 6-7 are examined herein.
Claims 5, and 8-10 are withdrawn (see restriction/election below).
Priority
This application is filed 07/12/2023 and claims the benefit of domestic priority as below:
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Access code of foreign applications is provided.
Information Disclosure Statements
Seven IDS(s) received on 7/12/2023, 10/31/2023, 12/15/2023, 3/12/2024, 11/13/2025, and 12/12/2025 have been considered unless marked with a strikethrough.
Election/Restrictions
Applicant elects group I, claims 1-4, and 6-7, directed to a benzoxazine compound represented by formula (1) and to a resin raw material composition or a curable resin composition comprising the compound. Applicant further elects the benzoxazine compound disclosed in Example 1 (paragraph [0027]) as the elected species in the reply filed on 1/9/2026 is acknowledged. Because applicant did not distinctly and specifically point out the supposed errors in the restriction requirement, the election has been treated as an election without traverse (MPEP § 818.01(a)).
Although no anticipatory art was found of the elected species, the Examiner expands the search pursuant to MPEP 803.02 because the elected species are not patentably distinct. See 35 USC §103 rejections below.
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 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 1-4, 6, and 7 are rejected under 35 U.S.C. 103 as being unpatentable over Wang et al. (US 2018/0030264 A1, pub’d 02/01/2018), in view of Musa et al. (“The effect of curing temperatures on the thermal behaviour of new polybenzoxazine‑modified epoxy resin” Polymer Bulletin, 2020, 77, 5439–5449, pub’d 11/22/2019).
With respect to independent claim 1, the claim recites to a benzoxazine compound comprising an aromatic backbone, terminal benzoxazine rings, and hydroxyl containing substituents, wherein the resulting composition exhibits low-temperature curing and high heat resistance.
Wang teaches low temperature curable benzoxazine compositions, including benzoxazine monomers and bis-benzoxazine systems derived from aromatic phenolic core (paragraph [0003], [0011], and claim 1). Wang further teaches curing temperatures of approximately 130-140oC (paragraph [0099], and the specific benzoxazine structures that have alkyl groups instead of hydroxy alkyl in N site substitutions (claim 3), thereby demonstrating that substituent structure affects curing behavior. For example, in the Formula (1a) of Wang, Z is CH2 or C(CH3)2, R is alkyl group, and R1 is hydrogen.
Wang fails to teach the specific structure of formula (1) as the instant claimed benzoxazine compounds that have hydroxy alkyl containing substituents attached at the nitrogen position
Musa teaches that a benzoxazine compound “BZ-OH” has utility as a component of a curable composition in the preparation of a cured polymeric product (scheme 1 page 5441, the abstract and conclusion section page 5447). Musa further teaches that hydroxy alkyl substituted benzoxazine compounds influence curing temperature and improve thermal behavior of polybenzoxazine based system. (conclusion section page 5447).
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Instant claim Formula (1)
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Wang’s Formula (1a)
Musa’s compound
The MPEP 2144.09 I states that:
“A prima facie case of obviousness may be made when chemical compounds have very close structural similarities and similar utilities. "An obviousness rejection based on similarity in chemical structure and function entails the motivation of one skilled in the art to make a claimed compound, in the expectation that compounds similar in structure will have similar properties." In re Payne, 606 F.2d 303, 313, 203 USPQ 245, 254 (CCPA 1979). See In re Papesch, 315 F.2d 381, 137 USPQ 43 (CCPA 1963) (discussed in more detail below) and In re Dillon, 919 F.2d 688, 16 USPQ2d 1897 (Fed. Cir. 1990)”
The MPEP 2144.09 II also states that:
“Compounds which are position isomers (compounds having the same radicals in physically different positions on the same nucleus) or homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties. In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977). See also In re May, 574 F.2d 1082, 197 USPQ 601 (CCPA 1978) (stereoisomers prima facie obvious).”
As set forth in MPEP 2144.09 I and II, it would have been obvious to a PHOSITA at the time of the invention to modify the benzoxazine compounds disclosed by Wang by substituting the alkyl N-substituents with hydroxy alkyl containing substituents as taught by Musa. The prior art compound is taught as having the same utility as those presently claimed. In view of the close relationship between the claimed compounds and the disclosed compound and the teachings of the combined references, there is good reason to provide for the corresponding homolog (modifying alkyl group to hydroxyl alkyl group) and to expect them to have the same or better properties including solubility. In order to archive the advantage of improved curing behavior and enhanced thermal performance while maintain low curing temperatures (paragraph [0010] in Wang, and abstract section in Musa).
Alternatively, it would have been prima facie obvious to start from the benzoxazine BZ-OH disclosed by Musa, and modify the linker by substituting the two methyl groups with hydrogen atoms as taught by Wang. Although Musa does not teach an anticipatory compound, one of ordinary skill in the art would have been motivated to make such a substitution because structurally similar compounds are expected to exhibit similar properties. In this case, both references relate to analogous art and the substitution would be expected to maintain the hydrophobic properties while providing a structurally related benzoxazine compound.
The references is directed to the same field of endeavor and address related to the application. The Supreme Court in KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 415-421, 82 USPQ2d 1385, 1395-97 (2007) identified a number of rationales to support a conclusion of obviousness which are consistent with the proper "functional approach" to the determination of obviousness as laid down in Graham.
Examples of rationales that may support a conclusion of obviousness include:
(A) Combining prior art elements according to known methods to yield predictable results;
(B) Simple substitution of one known element for another to obtain predictable results;
(C) Use of known technique to improve similar devices (methods, or products) in the same way;
(D) Applying a known technique to a known device (method, or product) ready for improvement to yield predictable results;
(E) "Obvious to try" – choosing from a finite number of identified, predictable solutions, with a reasonable expectation of success;
(F) Known work in one field of endeavor may prompt variations of it for use in either the same field or a different one based on design incentives or other market forces if the variations are predictable to one of ordinary skill in the art;
(G) Some teaching, suggestion, or motivation in the prior art that would have led one of ordinary skill to modify the prior art reference or to combine prior art reference teachings to arrive at the claimed invention.
Applying KSR example rationale (B) in the claim 1, it would have been prima facie obvious to a person having ordinary skill in the art to obvious to substitute one known benzoxazine N-substituent for another structurally similar and known N-substituent to obtain predictable improvement in curing kinetics and thermal properties.
With respect to claims 2-4, 6, and 7, Wang further teaches 1) a benzoxazine compound is used a resin raw material composition (paragraph [0109]-[0120]), as required in claim 2; 2) a benzoxazine compound forming part of a curable resin composition (claim 10, and 11), as required in claim 3; 3) a curable resin composition further comparing at least one selected from the group consisting of epoxy resins, benzoxazine compounds other than the benzoxazine compound represented by general formula (1), phenol resins, and bismaleimide compounds (paragraph [0005], and [0096]), as required in claim 4; 4) a curable resin composition comprising a resin raw material composition, and at least one selected from the group consisting of epoxy resins, benzoxazine compounds other than the benzoxazine compound represented by general formula (1), phenol resins, and bismaleimide compounds in the curable resin composition (paragraph [0095]-[0099], and claim 1), as required in claims 6 and 7.
Musa also reinstruct that the benzoxazine (10% by weight) was incorporated into a (50:50) weight ratio of epoxy resin and its hardener (abstract section), as required in claims 3, and 4. Musa further teaches curing temperatures, and thermal behavior for a polybenzoxazine‑modified epoxy resin (results and discussion section page 5444-5447).
Furthermore, claims 6 and 7 are not patentably district from claims 3 and 4, respectively. Claims 6 and 7 merely recite a curable resin composition comparing the resin raw material composition of claim 2, which itself comprises the benzoxazine compound of claim 1, and do not introduce any additional structural or functional limitations beyond those already recited in claims 3 and 4. Accordingly, claims 6 and 7 represent obvious variants of claims 3 and 4.
Applying KSR example rationale (B), it would have been prima facie obvious to a person having ordinary skill in the art to substitute of one known element for another structurally similar and modify the teaching of Wang and Musa to arrive at a reasonable expectation of results.
Conclusion
Claims 1-4, 6, and 7 are rejected.
Any inquiry concerning this communication or earlier communications from the examiner should be directed to SEONG JONG KIM whose telephone number is (571)272-6918. The examiner can normally be reached 7:00am-3:30pm.
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/SEONG JONG KIM/ Examiner, Art Unit 1621
/CLINTON A BROOKS/ Supervisory Patent Examiner, Art Unit 1621