DETAILED ACTION
Summary
Applicant’s amendment dated 2 March 2026 is acknowledged. Claims 1 and 4-8 are pending.
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
New grounds of rejection are necessitated by the amendment dated 2 March 2026. For this reason, this office action is properly made final.
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 Rejections - 35 USC § 103
Claims 1 and 4-5 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 90:10, 75:25, and 50:50 (Table 1) and 90:10, 75:25 and 50:50 (Table 2) which are all within the recited range. ANDERSON measures the glass transition temperatures for these examples and obtains values of greater than 291°C for the three examples in Table 1 and 286°C for Example 8 in Table 2. These all satisfy the requirement that the glass transition temperature is 250°C or more.
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 (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.
ANDERSON generally teaches that its compositions are 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 largely overlaps the 200°C-260°C range which is recited by the claim. ANDERSON exemplifies curing steps for benzoxazine (BFBZN)/diphthalonitrile (RDPN) blends (p. 33, Ex 1-3, Table 1) of 190°C, 220°C, 265°C and 300°C ramping the temperature between set points (p. 32, lines 26-35) which spans across the recited 200-260°C cure and 250-260°C post-cure steps and all have glass transition temperatures within the recited range. 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/RDPN blends that satisfy the compositional limitations of the Claim (p. 33, Ex 1-3, Table 1). Since the recited post-cure temperatures are the same as the recited cure temperatures, one could interpret a curing step within the recited range as including both cure and post-cure steps. It would be obvious to modify the invention of ANDERSON and cure and post cure the composition within the curing temperature range taught by ANDERON and is also within the 200°C-260°C range and 250°C-260°C range recited by the claim. Further, the compositions made obvious by ANDERSON in view of ISHIDA are presumed to have the characteristic of curability and post-curability at the recited temperature because ANDERSON in view of ISHIDA teach all of the structural limitations recited by the claim. It is well settled that where the prior art describes the components of a claimed compound or compositions in concentrations within or overlapping the claimed concentrations a prima facie case of obviousness is established. See In re Harris, 409 F.3d 1339, 1343, 74 USPQ2d 1951, 1953 (Fed. Cir 2005); In re Peterson, 315 F.3d 1325, 1329, 65 USPQ 2d 1379, 1382 (Fed. Cir. 1997); In re Woodruff, 919 F.2d 1575, 1578 16 USPQ2d 1934, 1936-37 (CCPA 1990); In re Malagari, 499 F.2d 1297, 1303, 182 USPQ 549, 553 (CCPA 1974). For more discussion see MPEP 2144.05-I.
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).
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 2 March 2026 have been fully considered but they are not persuasive.
Applicant argues that in the BFBZN/BMDPN blend examples (6-8) of ANDERSON either fail to reach the post-curing temperature of 250°C or they fail to obtain a glass transition temperature of 250°C for its BFBZN/BMDPN blends. In response, ANDERSON teaches PdBZN/RDPN Examples (1-3) which have include curing steps with pass through both of the curing and post-curing temperature zone and obtains high glass transition temperatures of 291-400°C.
Applicant argues that ANDERSON does not teach acetylene-bearing benzoxazine structures and the Examiner relies on ISHIDA for this feature, and it is not known how much the cure properties and glass transition temperatures reported by ANDERSON would be affected by the modification. It response, the claims do not recite a level of acetylenization in the benzoxazine compounds and no evidence has been presents as to whether the presence of acetylene groups would raise or lower the glass transition temperature.
Conclusion
Applicant's amendment necessitated the new ground(s) of rejection presented in this Office action. Accordingly, THIS ACTION IS MADE FINAL. See MPEP § 706.07(a). 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.
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/D.R.F./Examiner, Art Unit 1764
/KREGG T BROOKS/Primary Examiner, Art Unit 1764