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 .
Priority
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Status of Claims
The examiner acknowledges the amendment to claim 1 and the cancellation of claim 3. Claims 1-2 and 4-13 are pending.
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claims 1-2, 4, and 6-13 are rejected under 35 U.S.C. 103 as being unpatentable over Ueno (US 20170158854).
Regarding Claims 1 and 2,
Ueno teaches a composition that includes a polyphenylene ether with appended vinyl groups (Paragraph 23) of the following structure:
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86
570
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in which X is equal to:
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330
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and Y is equal to:
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which also contains a cyclic phosphazene (Paragraph 19) of the following structure:
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232
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where at least one of Z1 or Z2 is a vinyl group and in which n is an integer of 3 to 8 (Paragraph 22), which in an example preparation has n=3 (Paragraph 131) and where the average composition is 3 vinyl-containing aryl groups and 3 without. While Ueno does not explicitly call for the use of the ortho-substituted version, the notation used by Ueno to depict Z1 and Z2 would allow for this variation. Additionally, while Ueno does not explicitly call for the formation of a prepolymer, Ueno does teach that any known treatment may be performed (Paragraph 91) and also outlines a multistage curing process (Paragraph 92). One of ordinary skill in the art, seeking a more uniform composition with regard to the dispersion of the phosphazene component, would seek to premix or pre-react some of the components in order to achieve this outcome. As such, it would have been obvious to have formed a prepolymer prior to mixing of all components. Alternatively, in the absence of new or unexpected results, it has been held that the selection of any order of process steps is prima facie obvious. See MPEP 2144.04.IV.C.
Ueno teaches the use of curing accelerators, but does not teach the use of the specific compounds of the instant claim. However, Ueno does teach the use of a variety of peroxides and azo compounds such as AIBN, which are known to facilitate radical polymerizations. One of the disclosed structures of the instant claim is TEMPO, which is also a radical facilitator. Because the compounds taught by Ueno and those of the instant claim are known to be used for the same purpose, it would have been obvious to have substituted TEMPO for the radical initiators disclosed by Ueno. See MPEP 2144.06.II.
Finally, with regard to the measurement of the pH of an aqueous extract of the phosphazene, because the claim is directed towards a composition containing the phosphazene, the addition of a method for measuring the pH renders this claim to be a product-by-process claim. As such, only the product itself and its properties can be used to determine patentability. See MPEP 2113.I. Therefore, any phosphazene compound that meets the requirements of the instant claim will read upon the claim limitations.
While Ueno is silent on the pH of the phosphazene component, because the compound disclosed is substantially similar to those of the instant claims, it would necessarily follow that the pH of the compound would be the same. It has been held that "Products of identical chemical composition cannot have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). See MPEP 2112.01.II. Additionally, Ueno teaches that following the synthesis of the vinyl-containing cyclic phosphazene, an aqueous extraction is conducted while the compound is dissolved in toluene (Synthesis Example 3, Paragraph 126) prior to isolation, which would remove aqueous soluble material.
Regarding Claim 4,
Ueno teaches a multistep curing process (Paragraph 92), but is silent upon the conversion rate of the reaction. Ueno teaches a composition that results in a curable laminate (Paragraph 91), and it would logically follow that the conversion rate of the vinyl-modified polyphenylene ether and phosphazene would be within the described range in the final product. Additionally, the extent to which this reaction proceeds would alter the amount and chain length of the prepolymer relative to the total amount of material in the composition prior to curing. In effect, this change would alter the length of segments between the introduction of other components such as the ethylenically unsaturated monomer, other polymers in the composition, and crosslinking agents. As a result, the length of the reaction time and, by extension, the conversion rate, would constitute or result-effective variable, as the length of the prepolymer would increase the spacing between the aforementioned components and thus, properties such as strength and rigidity. Finally, based upon the size of the stated range of 10 to 99%, in the absence of unexpected results, this value cannot be considered critical. See MPEP 2144.05.I.
Regarding Claim 6,
Ueno teaches that epoxy-functionalized resins may be added to the composition (Paragraph 69) and notes the use of a variety of amines for use as curing accelerators (Paragraph 86).
Regarding Claim 7,
Ueno teaches the use of inorganic fillers (Paragraph 75), curing accelerators (Paragraph 86), silane surface treatment agents (Paragraph 83), flame retardants (Paragraph 85), and solvent (Paragraph 87).
Regarding Claim 8,
Ueno teaches that the composition may be used to make prepregs, resin sheets or circuit boards (Paragraph 91).
Regarding Claim 9,
Ueno teaches that the cured compositions have a dielectric loss tangent at 10 GHz of less than 0.005 (Examples 1-7, Table 1). While Ueno does not specify the conditions the material was subjected to prior to the test, as the composition of Ueno is largely similar to that of the instant claim, it would necessarily follow that cured composition would have largely similar properties. It has been held that "Products of identical chemical composition can not have mutually exclusive properties." In re Spada, 911 F.2d 705, 709, 15 USPQ2d 1655, 1658 (Fed. Cir. 1990). See MPEP 2112.01.II.
Regarding Claim 10,
Ueno teaches several examples that have a glass transition temperature over 250 °C (Examples 1-7, Table 1), meeting the requirement of the instant claim.
Regarding Claim 11,
Ueno teaches several examples (Page 15 - Examples 1-7, Table 1) in which the coefficient of thermal expansion is 50 ppm/ °C or less as measured by the JIS C6481 below the glass transition temperature and below 250 ppm/ °C above the glass transition temperature, which when converted to percentage is below 1%, meeting the requirement of the instant claim.
Regarding Claim 12,
Ueno teaches that the cured compositions have peel strength as measured according to JIS C6481 of greater than 0.8 kN/m, which is greater than 4.5 lb/in, meeting the requirement of the instant claim.
Regarding Claim 13,
Ueno teaches examples (Examples 1-7, Table 1) where no abnormalities occur after exposure to 121 °C at 2 atmospheres for 5 hours, followed by immersion in solder at 288 °C for 30 seconds, meeting the requirement of the instant claim.
Claim 5 is rejected under 35 U.S.C. 103 as being unpatentable over Ueno (US 20170158854) as applied to claims 1-4 and 6-13 above, and further in view of Koyama (JP2013-075386).
Ueno teaches a composition that contains the components of claim 1, however does not teach the addition of a vinyl group-containing monomer. Koyama teaches a similar composition for the purposes of making circuit boards and prepregs in which butadiene and styrene can be used (Page 17, Lines 15-33). Such components are typically used as reactive diluents, and one of ordinary skill in the art, seeking to reduce the viscosity of the composition for coating purposes without requiring the addition of volatile solvent that can pose health hazards would be motivated to add reactive diluents to accomplish this. As such, it would have been obvious to have used the reactive diluents as taught by Koyama in the resin composition of Ueno to obtain the predictable result of a lower viscosity composition that results in a cured resin.
Response to Arguments
Applicant's arguments filed 12/16/2025 have been fully considered but they are not persuasive for the following reasons.
On pages 1-3, the applicant argues that the Ueno does to teach or enable the ordinarily skilled artisan to infer the pH value of the cyclic phosphazene and further argues that Ueno’s procedure is neutralizing the solution as opposed to the phosphazene itself and is therefore not related to the surface pH of the phosphazene. The examiner disagrees. While the applicant refers to the “surface pH”, what the applicant’s procedure is actually measuring is simply the pH of any compounds that can be extract with an aqueous wash. In fact, the applicant’s specification refers to adding water, filtering, and then measuring the pH of the aqueous extract (Paragraph 100). Based upon the phosphazene structure, this compound would appear unlikely to have much, if any, aqueous solubility and would thus be determining the pH of the unwanted components. Functionally, this is performing an extraction in much the same way that the procedure of Ueno conducts. As Ueno is performing a liquid-liquid extraction with toluene containing a solubilized phosphazene, it would logically follow that any aqueous soluble and presumably charged species would be eliminated in this step. As such, the compound taught by Ueno which does not contain any acidic or basic functionality, would meet the “surface pH” requirement.
On pages 3-4, the applicant states that the ordinarily skilled artisan would not choose to use TEMPO-based compounds and further that TEMPO-based compounds do not function in the same fashion as other radical compounds. The examiner again disagrees. In fact, Nabifar (Chemical Engineering Science volume 64, pages 304-312 (2009), art not cited) shows that TEMPO can be used in polymerizations of styrene and further teaches that while narrower polydispersities are observed when using only TEMPO, a bigger improvement is noted when used in conjunction with a peroxide compound such as BPO (Page 312, conclusion paragraph). The latter is highly relevant to the applicant’s examples, as the exemplary examples all utilize a peroxide-based compound as well as a TEMPO-based compound. As Ueno states that curing accelerators can be chosen to adjust curing speed and that it is known in the literature that the addition of TEMPO-based compounds improves polydispersity of styrene-based polymers which is further known to result in more controlled material properties, it would have been obvious to have used such knowledge in this case as well.
Finally, on pages 4-5, the applicant argues unexpected results. However, noted above, the use of TEMPO-based compounds in the presence of peroxide-based initiators is known to reduce polydispersity of the resulting polymers and thus afford more defined material properties, it would logically follow that improvements would be expected when utilizing this technique.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Nabifar (Chemical Engineering Science volume 65, pages 304-312 (2009) teaches the use of TEMPO in polymerization of styrene monomers.
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.
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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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Heidi Kelley can be reached at 571-270-1831. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/A.J.B./Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765