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
This action is FINAL.
Claim Status
Claims 1-4, and 6-7 are examined herein.
Claims 5, and 8-10 are withdrawn (see the restriction in the non-final dated 2/24/2026 ).
Priority
This application is filed 07/12/2023 and claims the benefit of domestic priority as below:
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Information Disclosure Statement
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. One additional IDS received on 3/3/2026 also have been considered unless marked with a strikethrough.
Response to Arguments/Amendments
Applicant's arguments filed 4/28/2026 have been fully considered but they are not persuasive.
In the non-final dated 2/24/2026, claims 5, and 8-10 were withdrawn due to the restriction, and claims 1-4, and 6-7 were examined upon their merits.
In the non-final dated 2/24/2026, claims 1-4, and 6-7 were rejected under 35 U.S.C. 103. In response from Applicant, claim 1 is amended. No new matter has been added, and no cancelled claims.
Regarding the Claim Rejections under 35 USC § 103 for claims 1-4, and 6-7, Applicant's arguments filed on 4/28/2026 have been fully considered but they are not persuasive.
The rejection is based on the combined teachings of Wang and Musa, not on bodily incorporation of Musa’s entire epoxy/PBZ network into Wang. The obviousness analysis is supported by an articulated reason with rationale underpinning. MPEP 2143 states that a proper obviousness rejection requires articulated reasoning with some rationale underpinning why the results of the proposed combination would have been predictable to one of ordinary skill in the art. Musa is analogous art because it is in the same field of endeavor, namely benzoxazine containing curable resin compositions, and is at least reasonably pertinent to the problem addressed by Wang, including control of curing behavior and thermal properties of benzoxazine based curable materials.
Applicant’s amendment limiting the methylene linkage to an ortho or para position relative to the corresponding oxygen bonding position of each benzene ring has also been fully considered. However, the amendment does not overcome the rejection. Wang’s Formula (1a) in claim 3, as shown below, depicts a Z linkage at the para position relative to the aromatic carboned to the benzoxazine oxygen, and Wang expressly teaches that Z may be CH2. Thus, Wang teaches a para methylene linked aromatic bisbenzoxazine framework within the amended ortho or para positional limitation.
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Accordingly, the rejection does not require stacking a positional isomer rationale on top of a secondary reference substitution. The amended positional limitation does not introduce an additional structural difference over Wang because Wang already depicts the para linked embodiment and expressly permits CH2 as the Z linking group. The relevant structural difference between Wang and claim 1 remains the nature of the N-substituent on the benzoxazine ring. Musa is relied upon for the known hydroxyalkyl containing N-substituent and its known relevance to curing behavior and thermal properties in benzoxazine containing curable resin systems.
(a) Applicant argues that “Musa teaches that BZ-OH is useful as an intermediate to produce
the PBZ/epoxy network,” and that “Musa does not teach any utility of BZ-OH to produce “an organic sulfur acid-free composition containing a benzoxazine, phenolic compound and nitrogen containing heterocyclic compound” as taught by Wang.” Applicant also argues that “Wang does not use any PBZ/epoxy network nor ring-opening polymerization to produce the organic sulfur acid-free composition”, and that “the effect of curing temperature on the thermal behavior of epoxy resin modified with BZ-OH to form the PBZ/epoxy network of Musa is no proxy or a poor proxy for how effective of the hydroxyl end of BZ-OH on production of the organic sulfur acid-free composition of Wang which uses no PBZ/epoxy network”.
Applicant’s arguments have been fully considered but they are not persuasive. Applicant’s arguments are not commensurate with the basis of the rejection. Wang is relied upon as the primary reference because Wang teaches low-temperature curable benzoxazine compositions including benzoxazine compounds having an aromatic backbone and N-substituted benzoxazine rings. Wang’s Formula (1a) further depicts a para linked aromatic bisbenzoxazine framework, and Wang expressly teaches that Z may be CH2. Musa is relied upon for the additional teaching that hydroxyalkyl substituted benzoxazine compounds, including BZ-OH, were known in the benzoxazine resin art and were used in curable resin compositions that affect curing behavior and thermal properties.
The rejection does not rely on bodily Incorporating Musa’s entire epoxy/PBZ network into Wang, nor does the rejection require modifying Wang to include Musa’s epoxy resin system. Rather, Musa is relied upon for its teaching of a hydroxyalkyl substitution is relevant to curing and thermal behavior in benzoxazine containing curable compositions. The proposed modification is directed to the substituent structure of the benzoxazine compound, not to replacement of Wang’s overall curable composition with Musa’s epoxy network.
Although Musa evaluates BZ-OH in an epoxy containing system, Musa nevertheless teaches the structures and benzoxazine related function of BZ-OH, including its relationship to curing and thermal behavior. The rejection relies on that teaching, not on the epoxy resin matrix itself. This reasoning is consistent with MPEP 2141, which frames obviousness as an inquiry into the scope and content of the prior art, the differences between the claimed invention and the prior art, the level of ordinary skill in the art, and any objective evidence. MPEP 2141.01(a) also explains that prior art may be considered if it is in the field of endeavor or reasonably pertinent to the problem addressed. Because Wang seeks benzoxazine compositions having improved low temperature curability and Musa teaches that hydroxyalkyl substitution on benzoxazine compounds affects curing behavior and thermal properties, one of ordinary skill in the art would have had reason to use Musa’s hydroxyalkyl substituted benzoxazine teaching in Wang’s benzoxazine framework to obtain a benzoxazine compound expected to remain useful in low temperature curable resin compositions.
Accordingly, Applicant’s argument that Musa and Wang are directed to different resin systems does not overcome the rejection because the proposed combination relies on Musa for its teaching of a known hydroxyalkyl substituted benzoxazine structure and its known relevance to curing and thermal properties, not for incorporation of Musa’s epoxy/PBZ network into Wang.
(b) Applicant argues that “Wang recognizes that benzoxazines combined with epoxy resins
are known,” but that they “have a drawback of higher curing temperatures”. Applicant also argues that “Wang solves the above problem by using "an organic sulfur acid-free composition containing a benzoxazine, phenolic compound and nitrogen-containing heterocyclic compound", i.e., without using epoxy reins to form a network.”, and therefore “a person of ordinary skill in the art would not have any reason to modify the specific benzoxazine compound of Wang by replacing the alkyl group attached to nitrogen of Wang's formular (la) with (CH2)2OH of BZ-OH shown in Musa.
Applicant’s arguments have been fully considered but they are not persuasive. Applicant’s reliance on Wang’s discussion of epoxy drawbacks is also not persuasive. Wang’s discussion of drawbacks associated with epoxy/benzoxazine blends does not teach away from the proposed modification because the proposed modification does not add epoxy resin to Wang’s composition. Rather, the rejection proposes replacing Wang’s N-alkyl substituent with the known hydroxyalkyl substituent taught by Musa while retaining Wang’s benzoxazine framework and curable composition context. Thus, Wang’s discussion of drawbacks associated with epoxy blends does not criticize, discredit, or otherwise discourage the use of a hydroxyalkyl substituted benzoxazine compound. At most, Wang identifies drawbacks associated with epoxy containing benzoxazine blends. Wang does not criticize, discredit, or discourage hydroxyalkyl substitution on a benzoxazine compound. Therefore, Wang’s discussion of epoxy containing systems does not amount to teaching away from the proposed structural modification. (see In re Fulton, 391 F.3d 1195, 1201, 73 USPQ2d 1141, 1146 (Fed. Cir. 2004), and MPEP 2123/MPEP 2145)
Moreover, Musa provides a relevant teaching that hydroxyalkyl substituted benzoxazine compounds are known in the benzoxazine resin art and are relevant to curing and thermal behavior. Therefore, Wang’s disclosure of a low temperature curable benzoxazine composition and Musa’s disclosure of BZ-OH provide a sufficient reason to modify the N-alkyl substituent of Wang’s benzoxazine compound, notwithstanding Wang’s discussion of drawbacks associated with epoxy-containing blends.
MPEP 2144.09 recognizes that close structural similarity between chemical compounds having similar utilities may support a prima facie case of obviousness, although rebuttal evidence, including evidence of unexpected results or lack of a reasonable expectation of similar utility or properties, must be considered. Here, Musa does not merely disclose BZ-OH as an unidentified or utility less intermediate. Musa teaches BZ-OH in the context of benzoxazine containing curable resin compositions and evaluates curing and thermal behavior. Therefore, Musa provides a specific and relevant utility for the hydroxyalkyl substituted benzoxazine compound in the same general field of benzoxazine curable resin technology.
Accordingly, Applicant’s argument that Wang’s approach is successful without epoxy resin does not overcome the rejection because the proposed combination relies on Musa for its teaching of a known hydroxyalkyl substituted benzoxazine structure and its known relevance to curing and thermal properties, not for incorporation of Musa’s epoxy resin system into Wang.
Applicant argues that “the instant specification discusses Wang's formula (la) as
Comparative Example Compound B (par. 0029), and Musa's compound as Comparative Example Compound A, both of which are inferior to the claimed compound.” Applicant also argues that “From Table I and par. 0032, it is clear that the claimed compound cures at a lower temperature than Wang's formula (la) and Musa's compound, thereby reducing the temperature in the molding process of thermosetting resins, enabling increased efficiency” and “being usable even with heat-sensitive materials”. Applicant, therefore, argues that “the corresponding homolog (modifying alkyl group to hydroxyl alkyl group) and to expect them to have the same or better properties including solubility" is unwarranted and improper.”
Applicant’s arguments have been fully considered but they are not persuasive. As discussed above, MPEP 2144.09 provides that close structural similarity between chemical compounds, including homologs, analogs, and isomers, may support a prima facie case of obviousness where the compounds have similar utilities. The rationale is that compounds similar in structure are generally expected to have similar properties, while also recognizing that all relevant facts and rebuttal evidence must be considered.
Here, Wang and Musa teach structurally related benzoxazine compounds having similar utility in curable resin compositions. Wang teaches N-alkyl substituted benzoxazine compounds in low temperature curable benzoxazine compositions. Wang’s Formula (1a), as discussed above, depicts the relevant para linked aromatic benzoxazine framework, and Wang expressly teaches that Z may be CH2. Therefore, the amended ortho or para limitation does not create an additional distinction over Wang because the para alternative is taught by Wang. Musa teaches hydroxyalkyl substituted benzoxazine compounds in benzoxazine containing curable resin systems and discusses curing and thermal behavior. The claimed compound differs from the cited compounds principally by a structurally related N-substituent modification within the same benzoxazine compound class. In view of the close structural relationship and similar curable resin utility, one of ordinary skill in the art would have had reason to make the claimed modification with a reasonable expectation that the resulting compound would remain useful in curing benzoxazine resin compositions.
Applicant’s evidence of alleged unexpected results has been considered. MPEP 2145 requires consideration of rebuttal evidence and arguments, including evidence in the specification, and such evidence must be weighed with all evidence of obviousness and nonobviousness.
However, the evidence is not sufficient to overcome the prima facie case. Applicant relies on Table 1 and paragraph [0032] of the specification, which compare a single inventive Example 1 compound with comparative example compound A and comparative example compound B. Comparative example compound B corresponds to one compound within Wang’s Markush disclosure. However, claim 1 is directed to a Markush/genus of benzoxazine compounds, whereas Example 1 is only a single species within that genus.
Therefore, evidence limited to Example 1 does not, without additional data or persuasive technical reasoning, establish that the alleged lower curing temperature, heat resistance, or glass transition temperature advantage is reasonably commensurate in scope with the full breadth of claim 1. MPEP 716.02(d) states that objective evidence of nonobviousness, including unexpected results, must be commensurate in scope with the claims.
The present record does not establish such a trend, structure property relationship, or reasonable correlation sufficient to extend the results for the single Example 1 species to the full Markush/genus of claim 1. Applicant has not provided additional comparative data, a declaration under 37 CFR 1.132 or other evidence under MPEP 716, or persuasive technical reasoning showing that the alleged lower curing temperature, heat resistance, or glass transition temperature advantage would be obtained across the full scope of claim 1.
Applicant has also not established a sufficient nexus between the alleged superior results of Example 1 and the full scope of the claimed genus. The evidence does not show that the alleged advantages arise from a feature common to substantially all compounds encompassed by claim 1, rather than from the particular structure of the single tested species.
Accordingly, even if Example 1 exhibits certain advantages over the specific comparative compounds tested, the evidence does not establish that the asserted advantages are commensurate in scope with the breadth of claim 1. The data therefore do not outweigh the evidence supporting prima facie obviousness. Moreover, the alleged results relate to curing temperature and thermal properties, which are the same type of properties that Wang and Musa identify as relevant to benzoxazine curable resin systems. Curing behavior and thermal properties are known properties of concern in benzoxazine curable resin systems, as evidenced by both Wang and Musa. Thus, Applicant’s evidence relates to properties that the prior art already recognized as relevant and the alleged improvement must be supported by evidence sufficient to show unexpectedness across the claimed scope, and the property being optimized was known in the art, and the claimed modification represents the sue of a known benzoxazine substituent to affect known benzoxazine resin properties. Therefore, Application’s reliance on the alleged superiority of Example 1 is insufficient to overcome the prima facie case of obviousness.
Applicant argues that “despite the expectation that structurally similar compounds are
expected to exhibit similar properties as asserted by the Examiner, the structurally similar compound (modifying alkyl group to hydroxyl alkyl group) exhibits different and significantly better properties.” Applicant, therefore, argues that the Examiner's assertion that it would have been 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” is “unwarranted and improper”.
Applicant’s arguments have been fully considered but they are not persuasive. In the alternative, even starting from Musa, Wang provides a structurally related benzoxazine backbone in which Z may be CH2 at the para position, as depicted in Formula (1a). Thus, Wang would have suggested a para methylene linked aromatic benzoxazine framework while Musa supplies the hydroxyalkyl substituted benzoxazine teaching. The alternative rationale is not based on hindsight reconstruction but on the structural relationship between the benzoxazine compounds disclosed in the references and their similar utility in curable resin compositions. This alternative rationale is independent of, and does not alter, the primary rationale based on modifying Wang’s benzoxazine compound with Musa’s hydroxyalkyl substituted benzoxazine teaching.
For clarity, when the aromatic carboned to the benzoxazine oxygen is used as the reference position, the Z linkage depicted in Wang’s Formula (1a) is para to that oxygen bonded aromatic carbon. Wang also expressly identifies CH2 as a possible Z group. Therefore, Wang teaches the corresponding para-methylene linked variant within the amended claim language.
Wang teaches aromatic bisbenzoxazine structures having a linking group Z between the aromatic rings, and Wang depicts Z at the para position relative to the corresponding bonding positions of the respective oxygen atoms in Formula (1a) and expressly teaching that Z may be CH2 (claim 3). Thus, Wang teaches the corresponding para methylene linked variant. Musa teaches the hydroxyalkyl substituted benzoxazine BZ-OH. In view of these teachings, one of ordinary skill in the art would have had reason to modify Musa’s benzoxazine framework using the structurally related para methylene linked aromatic backbone taught by Wang to obtain another benzoxazine compound reasonably expected to retain curable resin utility.
MPEP 2144 recognizes that a rationale supporting obviousness may come from the references themselves, the knowledge generally available to one of ordinary skill in the art, scientific principles, or legal precedent. MPEP 2144 also reflects that the rationale need not be limited to the identical problems or advantage identified by Applicant. MPEP 2144.09 also states that structural similarity may support a prima facie case of obviousness and that such a case may be rebutted by persuasive evidence showing no reasonable expectation of similar properties or unexpected results.
Applicant’s argument that structurally similar compounds do not necessarily exhibit similar properties is insufficient for the reasons discussed above. A prima facie case based on structural similarity may be rebutted by persuasive evidence showing no reasonable expectation of similar properties or unexpected results. Here, however, Applicant’s evidence is limited to Example 1 and does not establish a trend, structure property relationship, or reasonable correlation sufficient to extend the alleged unexpected results to the full scope of claim 1.
Accordingly, the alternative rationale based on Musa in view of Wang remains proper.
Applicant argues that “unpredictable technology (such as chemistry) coupled with
unexpected results weighs in favor of nonobviousness”. Applicant also argues that “the superior effects of the claimed benzoxazine compound as compared with the benzoxazine compound disclosed in Wang and Musa are not predictable and effectively rebuts KSR example rationale (B) (simple substitution to obtain predictable results)” and that “It is surprising that replacing substituents of the chemical structures of the two inferior compounds (Wang's formula (la) and Musa's compound) would arrive at the claimed superior compound”.
Applicant’s arguments have been fully considered but they are not persuasive. MPEP 2143 identifies “Examples of rationales that may support a conclusion of obviousness include: (B) Simple substitution of one known element for another to obtain predictable results;” as an exemplary rationale supporting obviousness. Under that rationale, “Office personnel must articulate the following: (1) a finding that the prior art contained a device (method, product, etc.) which differed from the claimed device by the substitution of some components (step, element, etc.) with other components”, and support a conclusion that the claim would have been obvious by showing that the substitution of one known element for another yields predictable results to one of ordinary skill in the art.
Those findings are present here. First, Wang teaches the benzoxazine framework differing from the claimed compound by the N-substituent. More specifically, Wang depicts a para linked aromatic bisbenzoxazine framework within the amended ortho or para positional limitation. Second, Musa teaches the hydroxyalkyl substituted benzoxazine moiety and its relevance to curing and thermal behavior. Third, one of ordinary skill in the art could have made the substitution using ordinary benzoxazine synthesis principles. Fourth, because both substituents were known benzoxazine N-substituents used in curable resin systems, the resulting compound would reasonably have been expected to retain benzoxazine curable resin utility and to affect known curing and thermal properties.
Thus, the rejection is not premised on stacking positional isomer case law on top of an additional secondary reference substitution in an unpredictable art. Rather, Wang supplies the para CH2 linked benzoxazine framework, and Musa supplies the known hydroxyalkyl containing N-substituent. Therefore, the proposed modification is a substitution of one known benzoxazine N-substituent for another known benzoxazine N-substituent while retaining Wang’s para linked benzoxazine framework.
The rejection does not require a reasonable expectation that the modified compound would exhibit identical or superior curing temperature, heat resistance, or glass transition temperature relative to Applicant’s Example 1. Rather, the required expectation is that the modified benzoxazine compound would remain useful in benzoxazine containing curable resin compositions and would predictably affect curing and thermal behavior, which is supported by the combined teachings of Wang and Musa.
Applicant’s assertion that “it is well settled that unpredictable technology (such as chemistry) coupled with unexpected results weighs in favor of nonobviousness. Sanofi-Synthelabo v. Apotex, Inc., 550 F.3d 1075 (Fed. Cir. 2008).” However, MPEP 2143 explains that “obviousness does not require absolute predictability, but at least some degree of predictability is required. Evidence showing there was no reasonable expectation of success may support a conclusion of nonobviousness. In re Rinehart, 531 F.2d 1048, 189 USPQ 143 (CCPA 1976)”. Here, the prior art provides that degree of predictability because both references concern benzoxazine curable resin materials, curing/thermal property behavior, and structurally related benzoxazine compounds.
Applicant’s alleged unexpected results do not rebut the rejection because, as discussed above, the present record does not establish that the asserted advantages are commensurate in scope with claim 1. As discussed above, claim 1 is directed to a Markush/genus of compounds, whereas Example 1 is only one species within that genus. The specification compares only a single inventive Example 1 compound with two comparative compounds and does not provide sufficient evidence or persuasive technical reasoning establishing a trend, structure property relationship, or reasonable correlation applicable across the claimed Markush/genus. This is consistent with MPEP 716.02(d), which requires unexpected results evidence to be commensurate in scope with the claims.
Accordingly, the KSR rationale remains proper because the proposed modification constitutes the substitution of a known benzoxazine N-substituent for another known structurally related benzoxazine N-substituent, with a reasonable expectation of retaining curable resin utility and affecting known curing and thermal properties in a benzoxazine curable resin system.
Applicant argues that claim 1 has been amended to clarify that “the -CH2- is bonded to
the two benzene rings at their ortho or para positions relative to the corresponding bonding positions of the respective oxygen atoms". Applicant further argues that “at least in view of the foregoing, claim I would not have been obvious over Wang in in view of Musa. Claims 2-4, 6, and 7 also would not have been obvious at least due to their dependencies from claim I in addition to reciting further distinguishing features of particular utility.”
Applicant’s arguments have been fully considered but they are not persuasive. The amendment to claim 1 has been considered but does not overcome the rejection. Wang discloses benzoxazine structures in which the two aromatic rings are connected by Z, and Wang expressly defines Z as being “selected from a direct bond, CH2 , C(CH3)2, C=O, O, S, S=O, O=S=O, and other linking groups.” In Wang’s Formula (1a), the Z linkage is depicted at the para position relative to the aromatic carbon bonded to the benzoxazine oxygen (claim 3). Therefore, when Z is CH2, Wang teaches a pare methylene linked aromatic benzoxazine backbone within the amended ortho or para position limitation. at para position relative to the corresponding bonding positions of the respective oxygen atoms in Formula (1a) Thus, Wang expressly teaches a methylene linked aromatic benzoxazine backbone at para position when Z is CH2. Therefore, the amendment does not patentably distinguish claim 1 from Wang in view of Musa, and Applicant’s amendment does not create a new positional distinction over Wang.
Moreover, Applicant has not shown that the recited ortho or para positional relationship produces a result that is unexpected over Wang’s para methylene linked aromatic benzoxazine structure, nor has Applicant shown that such positional arrangements were unavailable or nonobvious to one of ordinary skill in the benzoxazine resin art. Applicant’s evidence of alleged unexpected results is directed to Example 1 and has not been shown to be reasonably representative of the full scope of claim 1, including the claimed ortho or para alternatives.
For the same reasons, dependent claims 2-4, 6, and 7 remain unpatentable. Claims 2-4, 6, and 7 depend from claim 1 and recite resin raw material compositions, curable resin compositions, and additional resin components such as epoxy resins, benzoxazine compounds, phenol resins, and bismaleimide compounds. Wang teaches benzoxazine compounds used in resin raw material and curable resin compositions, and teaches additional resin components in curable compositions. Musa further teaches incorporation of benzoxazine into epoxy resin systems and evaluates curing and thermal behavior of polybenzoxazine modified epoxy resin. Thus, the additional limitations of claims 2-4, 6, and 7 are taught or suggested by the combined references and do not overcome the rejection.
Accordingly, Applicant’s amendment and arguments do not overcome the prima facie case of obviousness.
Maintained Rejections
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 bisbenzoxazine 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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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.
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 SEONG JONG KIM whose telephone number is (571)272-6918. The examiner can normally be reached 7:00am-3:30pm.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Clinton A. Brooks can be reached at 571-270-7682. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/SEONG JONG KIM/ Examiner, Art Unit 1621
/CLINTON A BROOKS/ Supervisory Patent Examiner, Art Unit 1621
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