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 amendments to claims 1 and 11, the cancellation of claim 4, and the addition of claims 13-20. Claims 1-3, and 5-20 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 1-20 are rejected under 35 U.S.C. 103 as being unpatentable over Kawabata (US 20080318072, US Patent Application reference #2 from IDS dated 5/26/2023) as evidenced by Kopchik (EP 0076691).
Regarding Claims 1, 7-8, 11-12, 16, and 18-20
Kawabata teaches a polymer comprised of the following units (Abstract):
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in which R1 and R2 (corresponding to R1-R4 of the instant claims) can be hydrogen or alkyl groups of 1 to 8 carbons (Paragraph 41) and R3 can be hydrogen or an alkyl chain of 1 to 18 carbons (Paragraph 41), with this structure meeting the requirements of units 1 and 2 of the instant claim. Kawabata also teaches that R4 and R5 (corresponding to R5 and R6 of the instant claims) can be hydrogen or alkyl chains of 1 to 8 carbons (Paragraph 42) and that R6 (corresponding to R7 of the instant claims) can be an alkyl group of 1 to 18 carbons, a cycloalkyl group of 3 to 12 carbons, or an aryl group of 6 to 10 carbons (Paragraph 42). Additionally, Kawabata teaches that R7 (corresponding to R8 of the instant claims) may be a hydrogen or alkyl group of 1 to 8 carbons (Paragraph 43) and that R8 (corresponding to R9 of the instant claims) is an aryl group of 6 to 10 carbons (Paragraph 43). Kawabata also teaches that the resin is used to generate compositions (Paragraph 189) and may be used to form a polarizer film (Paragraph 139), meeting the requirements of the instant claims.
Regarding the amounts of each unit, Kawabata teaches that styrene (corresponding to M4 of the instant claim) preferably represents 15 to 25% (Paragraph 130) which is contained within the range of the instant claim and additionally that the amount of glutarimide units can be from 20 to 95%, but is preferably between 50 and 80% (Paragraph 97), which is contained within the range of the instant claims. While Kawabata does not teach the amounts of glutarimide units with hydrogen substituents separate from those with methyl substituents, Kawabata does teach that the imidization reaction can take place in a batch reactor or extruder (Paragraph 112) and that temperatures can be between 200 and 280 °C (Paragraph 121). These conditions are broadly similar to those of the instant application (Specification Paragraph 73). As both Kawabata and the instant application use ammonia under similar reaction conditions, it would logically follow that the composition of Kawabata would have M1 and M2 unit values that are similar. Further, the formation of glutarimide groups using ammonia when the starting polymer includes methyl esters of acrylates and methacrylates is known to afford both H and methyl-substituted imides, as evidenced by Kopchik, who teaches that the standard methods of forming imide polymers using ammonia cannot be done without the formation of some imide groups containing methyl substitution (Column 1, Lines 33-34) and further teaches an alternative method to formation of glutarimide polymers that does not result in the formation of methyl-substituted imides (Column 5, Lines 8-13). Because Kopchik notes that the formation of methyl-substituted imides occurs due to side reactions, it would logically follow that under standard reaction conditions using a polymer containing methyl esters of the acrylate/methacrylate monomer that are imidized to levels as required by the instant claims that some methyl substitution would be observed and would be present in amounts lower than the H-substituted imides and due to the levels of imidization taught by Kawabata, that the amount of M1 would be greater than 7 mol%.
As such, despite Kawabata’s silence on the amounts, the composition of Kawabata would meet the requirement based upon the similar materials and reaction conditions when incorporating the knowledge that methyl-substituted imides occur in imidization reactions with ammonia due to side reactions as evidenced by Kopchik. It would therefore have been obvious prior to the effective filing date of the instant application to have set the amount of M1 and M2 to be greater than 0.
Regarding Claims 2 and 3,
Kawabata teaches that the orientation birefringence of the resin is between -0.1 and 0.1x10-3 (Paragraph 40), meeting the requirements of the instant claims.
Regarding Claim 5,
Kawabata teaches that the glass transition temperature is preferably greater than 130 °C (Paragraph 101) and demonstrates several examples meeting the requirement of greater than 124 °C of the instant claim (Table 1, Examples 1-13).
Kawabata also teaches that the methacrylate-polystyrene polymer can be imidized to form the imide resin (Paragraph 109) with preferable imidizing agents including ammonia (Paragraph 119). Kawabata also teaches the use of Estyrene MS-800 as the methacrylate-polystyrene polymer (Paragraph 244) and further states that this polymer has styrene content of 20% (Paragraph 286), meeting the requirement of the instant claims.
Regarding Claim 6,
Kawabata is silent on the 5% weight loss temperature. However, Kawabata does teach that the reaction temperature for imidization should be below 400 °C, more preferably below 280 °C to avoid decomposition of the resin (Paragraph 220). As such, it would logically follow that the decomposition temperature of the resin would be above 400 °C based upon this information. Further, as the composition taught by Kawabata is comprised of the same components as that of the instant application as well as using overlapping amounts of these components, it would necessarily follow that the composition would have similar decomposition temperatures as well. "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 Claims 9 and 10,
Kawabata teaches that the composition may be used as a molded product (Paragraph 79) or a polarizer-protective film (Paragraph 139). Further, Kawabata teaches that the polarizer protective film may be subjected to a coating treatment (Paragraph 154), which it would logically follow that by disclosing a molded item as well as the ability to be coated would read upon a substrate and stacking of film layers. Further, Kawabata teaches that films made of the resin can also be used in the formation of conductive materials in which an ITO layer is deposited on the film (Paragraph 179). While Kawabata does not explicitly disclose the conductive film as described in the instant claim, because Kawabata discloses additional coatings on the film as well as the deposition of electrically-conductive layers to form a similar article, it would logically follow that these aspects could be combined in order to obtain a film stack as required by the instant claims. It would therefore have been obvious prior to the effective filing date of the instant application to have used the composition as disclosed by Kawabata in an electrically-conductive film stack as described in the instant claims.
Regarding Claims 13-15,
Kawabata is silent on the acid value and carboxylic acid content of the polymer. However, as Kawabata teaches that the non-imidized acrylate/methacrylate monomers are only allowed to be alkyl esters (Abstract), it would logically follow that Kawabata teaches that little to no acid be present in the final polymer. Further, Kawabata teaches that solvents such as ethanol and methanol is added (Paragraph 117), which at the elevated temperatures present in the imidization reaction (preferred to be 200-280 °C, Paragraph 121) would be able to esterify any acid formed. As such, it would have been obvious prior to the effective filing date of the instant application to have little to no acid groups present in the final polymer.
Regarding Claim 17,
Kawabata teaches the use of alcohols such as ethanol and methanol are added during the imidization reaction (Paragraph 117), which are noted in the applicant’s specification to be esterification agents (Paragraph 81).
Response to Arguments
Applicant's arguments filed 4/28/2026 have been fully considered but they are not persuasive for the following reasons.
On pages 8 and 9, the applicant argues that the amendments to claim 1 render the claims no longer anticipated by Kawabata. The examiner agrees and the rejection has been updated accordingly.
On page 9, the applicant argues the advantageous effects of having a greater amount of H-substituted imide than methyl-substituted imide. The examiner notes however that the applicant has not demonstrated that composition as taught by Kawabata would not meet this requirement. Further, the applicant argues on page 10 that the values of M1 and M2 would not be the same in the polymer taught by Kawabata because Kawabata does not mention the ratio. The examiner disagrees, and notes the evidence provided by Kopchik, which points out that methyl-substituted imide is necessarily formed when using ammonia due to a side reaction that occurs under standard conditions, which is noted in the rejection above. As such, while the applicant argues that simply using similar reaction conditions does not result in similar ratios between these two units, the prior art appears to disagree. While the applicant points to an example in which the methyl-substituted imide is present in larger quantities, this occurs at an ammonia level (10% by weight) which is below the amounts used in the examples by Kawabata (20-40% by weight, Table 1), which would not be analogous.
On page 11, the applicant argues that Kawabata does not teach the amount of ammonia or how it effects the relative amounts of monomer M1 to M2. The examiner notes that the amount of ammonia is not a requirement of the instant claims and that further, the amounts of imidization reagent used in the examples of Kawabata (20-40% by weight) falls within the ranges disclosed by the applicant’s original specification of 0.5 to 100 parts by weight (Paragraph 65). As previously stated, because the reaction conditions of Kawabata overlap with those of the instant application, it would logically follow that these conditions would result in a ratio of M1 to M2 similar to those of the instant application. While the applicant argues that broad ranges do not invite routine optimization, the examiner again notes that the formation of methyl-substituted imide is due to a side reaction as noted above, and as such, under the broadly similar conditions used by Kawabata, including those in the examples, the ordinarily skilled artisan would expect to obtain broadly similar results.
In summation, while the applicant argues that Kawabata’ silence on the ratio of M1 to M2 demonstrates novelty over the prior art, the examiner points towards the evidence of Kopchik that it is well known in the art that some amount of methyl-substituted imide is unavoidable under standard reaction conditions when using methyl acrylate/methacrylate as the monomer for imidization and that because the methyl variant forms due to a side reaction, that it would necessarily be a lesser component, especially at the higher imidization agent levels utilized by Kawabata. Therefore, the rejection is maintained.
Conclusion
The prior art made of record and not relied upon is considered pertinent to applicant's disclosure. Hallden-Abberton (Chapter 1 pages 3-9, Polymer modification, published 1997) teaches the alkyl-oxygen cleavage mechanism that is operative when reacting alkyl acrylate/methacrylate monomers with amines at elevated temperatures in an extruder, which demonstrates the alkylation of the amine by the ester under these conditions.
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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/A.J.B./Examiner, Art Unit 1765
/JOHN M COONEY/Primary Examiner, Art Unit 1765
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