DETAILED ACTION
Summary
This is a non-final office action for application 17/772,283. The amendment in the RCE dated 10 June 2026 is acknowledged.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office 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 .
Continued Examination Under 37 CFR 1.114
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on 10 June 2026 has been entered.
Claim Rejections - 35 USC § 103
Claims 1, 4-5 and 9-10 are rejected under 35 U.S.C. 103 as being unpatentable over ANDERSON (WO-2017105890-A1) in view of ISHIDA (WO-9918092-A1).
Regarding Claim 1, ANDERSON teaches a resin blend of a benzoxazine resin and a phthalonitrile resin (Abstract). ANDERSON teaches that each of these resins cures with heat (p. 10, lines 6-12) which makes them thermosetting resins. ANDERSON teaches that the weight ratio of its benzoxazine and phthalonitrile resins are broadly from 1:99 to 98: 2, or 4:96 to 95:5, which encompasses the recited ratios, or 15:85 to 85:15 or 75:25 to 25:75, which overlaps the recited ratios (p. 12, lines 13-16). ANDERSON exemplifies ratios of 50:50, 75:25 and 90:10 (Table 1), 50:50 (Table 2), 75:25 (Table 3; Table 4) which are all within the recited range of 1:1 to 10:1 and have glass transition temperatures above 250°C.
For the structural limitation on the phthalonitrile structure, ANDERSON teaches that its phthalonitrile resin may satisfy formula IV (p. 13, lines 12-15):
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where y is at least 1, and R is selected from groups which include biphenol and bisphenol (p. 13, lines 16-18). A phthalonitrile formed from biphenol or bisphenol would satisfy the requirement of the claim where R-groups are all hydrogens and Z is either a direct bond or a dimethyl-methylene group. ANDERSON exemplifies bisphenol T diphthalonitrile (BTDPN) and bisphenol M diphthalonitrile (BMDPN) (p. 30, Table; Tables 2-4).
ANDERSON teaches that its benzoxazine compounds are a broad class of substituted components on a benzoxazine group (p. 4, lines 5-10):
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which includes single benzoxazine rings, or may refer to polybenzoxazine compounds having two or more benzoxazine rings (p. 4: lines 11-12), that is, its benzoxazine resin may be a monofunctional benzoxazine or a multifunctional benzoxazine (p. 13, lines 8-9). ANDERSON does not specifically teach that its benzoxazine resins are acetylene-bearing. ISHIDA, in an invention of benzoxazine monomers oligomer and polymers (Abstract) teaches that pendant functional groups can be added to benzoxazine units to improve the thermal stability of the cured product, act as more effective flame barriers or result in higher amounts of char (Abstract). ISHIDA teaches that these pendant groups form thermally stable crosslinks and include acetylene (p. 2, 14-18) and includes alkynyl groups in its Markush definitions (p. 6, line 31-35; p. 7, 1-5). ISHIDA exemplifies a benzoxazine substituted with an ethynylphenyl group which is formed from phenol, formaldehyde and 3-aminophenylacetylene (Example A, p. 16, lines 19-29).
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It would be obvious to one of ordinary skill in the art at the time of the effective filing date of the current invention to modify the invention of ANDERSON with the teachings of ISHIDA and use benzoxazines substituted with alkynyl groups for the purpose of creating crosslinking locations and improving the thermal stability of the cured product, act as more effective flame barriers or result in higher amounts of char.
For the structural limitation on the benzoxazine structure, ISHIDA teaches the acetylene-bearing benzoxazine compounds where the exemplified structure (Example A, p. 16, lines 19-29) satisfies the recited structure where b=1, R1-R5 is hydrogen and R6 is an ethynylphenyl group which is an alkynyl-substituted C8-C20 aryl group.
The claim is directed to a composition which ‘is curable when subjected to’ the recited curing and post-cure steps and not a method with the recited cure steps, so the recited cure steps have less patentable weight. ANDERSON generally teaches that its compositions are curable when heated to a temperature of between about 50°C and 300°C, preferably between about 130°C-250°C (p. 24, lines 6-9). This overlaps the about 220°C or less to 250°C-260°C range which is recited by the claim. ANDERSON exemplifies curing steps for benzoxazine (BFBZN)/diphthalonitrile (BMDPN) blends within the recited range (p. 34-35: Ex 8; Table 2). ANDERSON teaches that a post cure step may be required for some compositions (p. 24, lines 9-11), but does not exemplify a post-cure step for the BFBZN/BMDPN blends that satisfy the compositional limitations of the claim, but note that ANDERSON teaches initial cure steps below 220°C and a maximum curing temperature of 240-250°C for several examples, including Ex 8 (p. 34, lines 31-34 Table 2) and Ex 14 (p. 37, lines 1-2 Table 4). One can interpret the final curing step of the multi-step cures taught by ANDERSON as being a post-cure steps. Compositions which are curable when subjected to the recited cure and post-cure steps are within the scope of the teachings of ANDERSON.
Regarding Claim 4, modified ANDERSON teaches the invention of Claim 1. ANDERSON teaches that its benzoxazine resin may be a monofunctional benzoxazine or a multifunctional benzoxazine (p. 13, lines 8-9). ANDERSON also teaches that its composition may contain more than one benzoxazine resin (p. 15, lines 9-13; p. 29, lines 15-16,19-20; Claim 12). It would be obvious to modify the invention of ANDERSON, if needed and include additional benzoxazine resins based on the teachings of its specification.
Regarding Claim 5, modified ANDERSON teaches the invention of Claim 1. ANDERSON teaches curing its composition (p., 24, lines 12-15; p. 32, line 31).
Regarding Claim 9, modified ANDERSON teaches the invention of Claim 1 where ISHIDA makes obvious the use benzoxazines substituted with alkynyl groups. ISHIDA generally teaches that its benzoxazines are formed by a reaction of phenolic compounds, formaldehydes and amines, desirably aromatic amines (p. 2, lines 25-26). ISHIDA teaches a variety of phenols, including phenol and 2-allyphenol (p. 5, lines 17-18). ISHIDA teaches in its first Example A, a benzoxazine formed from phenol, formaldehyde and 3-aminophenylacetylene (p. 16, lines 20-22) which is phenol 3-aminophenyl acetylene benzoxazine which is one of the recited acetylene-bearing benzoxazine compounds.
Regarding Claim 10, modified ANDERSON teaches the invention of Claim 1 where ANDERSON exemplifies ratios of 75:25 and 90:10 (Table 1) which are within the recited range of 1.5:1 to 10:1 and have glass transition temperatures above 250°C.
Claims 6-8 are rejected under 35 U.S.C. 103 as being unpatentable over ANDERSON (WO-2017105890-A1) in view of ISHIDA (WO-9918092-A1) as applied to Claim 1 above, and further in view of TRAN (WO-2012015604-A1).
Regarding Claim 6, modified ANDERSON teaches the invention of Claim 1. ANDERSON teaches that its composition is used in article manufacturing (p. 2, 22-24) but does not teach a process of comprising the recited steps of involving a layer of reinforcement fibers. TRAN, in an invention of a benzoxazine-based thermosetting resin (Abstract), teaches a process for producing a flame-retarded composite article which matches the recited steps ([0040], Claim 14). It would be obvious to one of ordinary skill to modify the invention of ANDERSON with the teachings of TRAN and use its composition in a process for producing a flame-retarded composite article for the purpose of obtaining flame-retarded composite articles.
Regarding Claim 7, modified ANDERSON teaches the invention of Claim 1. ANDERSON teaches that its composition is used in article manufacturing (p. 2, 22-24) but does not teach an RTM system. TRAN, in an invention of a benzoxazine-based thermosetting resin (Abstract), teaches a method for producing a flame-retarded composite article in an RTM system which matches the recited steps ([0042]). It would be obvious to one of ordinary skill to modify the invention of ANDERSON with the teachings of TRAN and use its composition in a method for producing a flame-retarded composite article in an RTM system for the purpose of obtaining flame-retarded composite articles.
Regarding Claim 8, modified ANDERSON teaches the invention of Claim 1. ANDERSON teaches that its composition is used in article manufacturing (p. 2, 22-24) but does not teach an VaRTM system. TRAN, in an invention of a benzoxazine-based thermosetting resin (Abstract), teaches a method for producing a flame-retarded composite article in an VaRTM system which matches the recited steps ([0043]). It would be obvious to one of ordinary skill to modify the invention of ANDERSON with the teachings of TRAN and use its composition in a method for producing a flame-retarded composite article in an VaRTM system for the purpose of obtaining flame-retarded composite articles.
Response to Arguments
Applicant's arguments filed 10 June 2026 have been fully considered but they are not persuasive.
Applicant argues that ANDERSON does not teach or suggest a separate post-cure step in the claimed 250-260°C range. In response, the claims are directed to a composition and not a method. The claims recite that the polymerizable composition ‘is curable when’ subjected to the recited initial cure and post-cure steps which gives this limitation less patentable weight. ANDERSON generally teaches that its compositions are curable when heated to a temperatures of between about 50°C and 300°C, preferably between about 130°C-250°C which overlaps with the recited curing conditions. ANDERSON teaches several examples with ramped cures having multiple curing steps at or below 220°C and a final curing temperature of 240-260°C, including Ex 5-8 (p. 34), Ex. 10 (p. 35) and Ex. 14-15 (p. 37). The final step of a ramped cure can be interpreted as a post-cure step. Curing profiles that start below 220°C and do not exceed 260°C are within the scope of the teachings of ANDERSON.
Applicant argues that ANDERSON teaches that phthalonitrile blends require cure temperatures above 250°C to reach high glass-transition temperatures. In response, the cited teaching of ANDERSON where higher post-cures at elevated temperatures may be required to achieve ultimate performance is for blends containing a greater portion of phthalonitrile resin. Since the claims recite ratios of benzoxazine to phthalonitrile of 1:1 to 10:1, a skilled user would not consider teachings for blends of greater amounts of phthalonitrile. In the same paragraph ANDERSON generally teaches preferable curing temperatures of 130-250°C. ANDERSON teaches several examples which obtain higher glass transition temperatures with maximum cure temperatures of 260°C or below, including Examples 8, 10 and 14 (p. 34-35 and 37; Tables 2 and 4).
Conclusion
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/D.R.F./Examiner, Art Unit 1764
/KREGG T BROOKS/Primary Examiner, Art Unit 1764
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