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 .
Drawings
The drawings are objected to because the text in figures 4 and 5 is blurry. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
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 1-9, 33, and 46 are rejected under 35 U.S.C. 103 as being unpatentable over Ishida (US 6,225,440) in view of Liu (Journal of Polymer Science Part A: Polymer Chemistry volume 43, (2005) pages 5267-5282).
Regarding Claims 1-9 and 33,
Ishida teaches benzoxazine resins that are of the following form:
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Where the R1 group (equivalent to the X group of the instant claims) can be represented by the following structure:
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which includes two CF3 groups in the X group. Ishida also teaches that the number of repeat units can be 2, 3, or 4 (Column 2, Lines 37-38) and that substituents on the aromatic ring can be hydrogen or alkyl groups, including fluorine substituted versions (Column 3, Lines 40-47) but demonstrates all these substituents being hydrogen in the structure above, meeting the requirements of claims 2, 5, 7, and 9. Ishida further teaches that the R2 group attached to the nitrogen can be an aromatic substituted alkyl group (Column 3, Lines 28-31). While Ishida teaches that an aromatic substituted alkyl group, Ishida does not teach that the aromatic group is a furan. Liu teaches using a furan-substituted alkyl group on the nitrogen of the benzoxazine to generate structure of the following type:
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which Liu teaches is done in order to form additional linkages in the polymer to enhance the glass transition temperatures and thermal stability of the resulting polymer (Pages 4268, right column, second paragraph) that Liu further teaches can be over 300 °C for the above structure after curing (Table 1). This increase in thermal stability and glass transition temperature affords the ordinarily skilled artisan with the motivation to substitute the aromatic furan for a standard aromatic group in the benzoxazine with a reasonable expectation of success. It would therefore have been obvious prior to the effective filing date of the instant application to have combined the teachings of Ishida and Liu.
With regard to fluorine content, Ishida in view of Liu teaches a structure that would be the same as the BPA-FBz structure except that the methyl groups in between the aromatic rings would be CF3 groups. On this basis, the molecular weight of the structure would be 552, of which 114 of the mass is fluorine, which is 20%, meeting the requirements of claims 1 and 3.
Regarding Claim 46,
Ishida teaches that the curing can take place at temperatures up to 300 °C (Column 5, Lines 25-28). One of ordinary skill in the art would be aware that the curing reaction can be monitored by a variety of techniques and would logically run the curing reaction to completion in order to obtain the full strength and stable properties of the cured composition.
Claims 14, 34, and 45 are rejected under 35 U.S.C. 103 as being unpatentable over Ishida (US 6,225,440) in view of Liu (Journal of Polymer Science Part A: Polymer Chemistry volume 43, (2005) pages 5267-5282) as applied to claims 1-9, 33, and 46 above, and further in view of Ward (US 20150175746).
Regarding Claims 14 and 45,
Ishida in view of Liu teaches the required benzoxazine as well as the glass transition temperature as discussed above in regard to claims 1 and 6. However, Ishida in view of Liu fails to teach the use of fiber reinforcement. Ward teaches that benzoxazine resins, including those taught by Ishida, can be combined with reinforcing fibers such as glass and carbon fibers (Paragraph 55) to form a composite material. While Ward does not specify the amount of resin or fiber, Ward does teach that the combination can be used to form a prepreg (Paragraph 56), which it would logically follow would have an amount of resin and fiber that meet the requirements of the instant claims. One of ordinary skill in the art, recognizing that Ward uses similar benzoxazines to those of Ishida in compositions that include reinforcing fibers that fibers could be used to reinforce cured compositions from resins of Ishida in view of Liu. As such, it would have been obvious prior to the effective filing date of the instant application to have added the reinforcing fibers taught by Ward in compositions using the resin of Ishida in view of Liu to obtain the predictable result of a fiber reinforced polybenzoxazine with a reasonable expectation of success.
Regarding Claim 34,
Ishida in view of Liu teaches a variety of linking groups, including those derived from bisphenol A and containing sulfonyl groups (Structures in Columns 3 and 4), Ishida in view of Liu does not teach the group linking the aromatic groups to be an oxygen. Ward teaches the use linking groups such as those listed from Ishida as well as an oxygen linkage (Paragraphs 25, 40). Because Ward teaches these groups to be used for the same purpose, it would have been obvious to have used an oxygen linked compound. See MPEP 2144.06.II
Claims 47-52 are rejected under 35 U.S.C. 103 as being unpatentable over Ishida (US 6,225,440) in view of Liu (Journal of Polymer Science Part A: Polymer Chemistry volume 43, (2005) pages 5267-5282) as applied to claims 1-9, 33, and 46 above, and further in view of Jones (WO 2022243655).
Regarding Claims 47-52,
Ishida in view of Liu teaches the curing of benzoxazines at elevated temperatures, with Liu teaching a stepwise cure at 160 °C followed by a second step at 200°C and finally at 240 °C (Page 5269, right column, preparation of polybenzoxazines paragraph), meeting the requirements of claim 51. It would have been obvious prior to the effective filing date of the instant application to have used the method of curing taught by Liu in combination with Ishida because both Ishida and Liu teach similar benzoxazine resins that are cured in the same temperature range with Liu providing a more detailed procedure. Ishida in view of Liu teaches glass transition temperatures that meet the requirements of claim 52 as discussed above in regard to claims 6 and 45. However, while Ishida teaches the use of catalysts such as boron trifluoride, boron trichloride, titanium tetrachloride and aluminum trichloride (Column 5, Lines 60-67), Ishida does not teach the use of iron(III) chloride. Jones teaches the use of the listed catalyst as well as iron(III) chloride (Page 13 Line 28-Page 14 Line 4). Jones further teaches that increasing amounts of catalyst increase the curing rate Page 48 Line 34-Page 49 Line 4) and mentions specifically a 3% catalyst loading (Page 49 Lines 1-2). Because Jones teaches iron(III) chloride to be used for the same purpose as the catalysts taught by Ishida, it would have been obvious prior to the effective filing date of the instant application to have substituted iron(III) chloride for the catalysts taught by Ishida. See MPEP 2144.06.II.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to ADAM J BERRO whose telephone number is (703)756-1283. The examiner can normally be reached M-F 8:30-5.
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/A.J.B./Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765
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