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 .
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claims 1, 4, 6-10, and 14-16, are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Hirota (JP 2008308551 A, Cite No. 3 on 4/26/2024 IDS, English translation provided).
Regarding claims 1, 4, 6-10, and 14-16, Hirota discloses a polyamic acid varnish (claim 1) ([0038]). Hirota further discloses using the polyamic acid as an adhesive by forming a film on a substrate and curing the film to form a polyimide, which can be used as a base film, a cover film, or an adhesive film used in circuit materials (claims 14-16) ([0040]). Hirota exemplifies preparing a polyimide film from polyamic acid ([0048]). In Example 2, Hirota reacts 0.322 moles of 4,4’-oxydiphthalic dianhydride (OPDA), 0.219 moles of 1,12-diaminododecane (DODA), and 0.094 moles of 1,3-bis(3-aminophenoxy)benzene (APB) ([0054], [0060], and Table 1).
DODA reads on instant monomer (A) that has a linear alkylene group having 12 carbon atoms and no ester bond, amide bond, or ether bond. The content of the monomer (A) is about 34 mol% based on a total amount of the monomer constituting the polyamic acid (0.219/(0.322+0.219+0.094)=0.219/0.635=0.344).
APB and OPDA read on a monomer (B) other than the monomer (A). The monomer (B) contains 100 mol% of an aromatic monomer (both OPDA and APB have aromatic groups). The aromatic monomer contains about 51 mol% (0.322/0.635=0.507) of an aromatic tetracarboxylic dianhydride having a diphenyl ether skeleton (OPDA) (claim 4). The monomer (B) contains an aromatic diamine having a diphenyl ether skeleton having three aromatic rings (APB) (claims 6-7). APB is 1,3-bis(3-aminophenoxy)benzene (claim 9) and reads on Formula (2) where X is an arylene group having 6 carbon atoms and n is 1 (claim 8).
The molar ratio between the diamine and the tetracarboxylic dianhydride is about 0.97 ((0.219+0.094)/0.322=0.313/0.322=0.97), reading on claim 10.
Claims 1-6 and 11-16 are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Oki (JP 2017203980 A, Cite No. 5 on 4/26/2024 IDS, English translation provided).
Regarding claims 1-3 and 14, Oki discloses a polyamic acid that is the reaction product of a tetracarboxylic dianhydride and a diamine ([0026]) and is used as a varnish ([0004] and [0199]). Oki further discloses a polyimide (claim 14) obtained by imidizing the polyamic acid ([0026]).
In Example 5, Oki discloses a tetracarboxylic dianhydride that is 50 mol%
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where m is 8 and 50 mol%
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119
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(Table 1 in [0200]). The diamine component for this example is
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79
240
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(Table 1). For this example, AN-4-17 reads on monomer (A) and AN-4-5 and DI-13-1 read on monomer (B). Monomer (A) is present in an amount of 25 mol% based on a total amount of the monomer constituting the polyamic acid. Monomer (B) contains 100 mol% of an aromatic monomer.
In example 11, Oki discloses a tetracarboxylic dianhydride that is 100 mol%
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where m is 8 (Table 1 in [0200]). The diamine component for this example is 50 mol%
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85
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and 50 mol%
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(Table 1). For this example, AN-4-17 reads on monomer (A) and DI-4-1 and DI-5-9 read on monomer (B). Monomer (A) is present in an amount of 50 mol% based on a total amount of the monomer constituting the polyamic acid. Monomer (B) contains 100 mol% of an aromatic monomer.
AN-4-17 reads on monomer (A) has a linear alkylene group having 8 carbon atoms and has no ester bond, amide bond, or ether bond. AN-4-17 also reads on a tetracarboxylic dianhydride (A1) with formula (1) where m is 8 (claims 2-3).
Regarding claims 4-5, Oki discloses the polyamic acid varnish of claim 1. Example 5’s dianhydride component comprises 50 mol% of AN-4-5. AN-4-5 is an aromatic tetracarboxylic dianhydride having a biphenyl skeleton.
Regarding claim 6, Oki discloses the polyamic acid varnish of claim 1. Example 11’s diamine component comprises DI-5-9, reading on wherein the aromatic monomer contains an aromatic diamine (B2) having a diphenyl ether skeleton.
Regarding claim 11, Oki discloses the polyamic acid varnish of claim 1.
Oki is silent as to the dissolution ratio of a polyimide film prepared from the polyamic acid varnish.
However, the examples in the instant specification demonstrate the properties of polyimide films prepared from polyamic acid varnishes. Of the instant examples, only Comparative Examples 1-2 do not satisfy the claimed dissolution ratio. Comparative Examples 1-2 are derived from pBAPP and either a 0.8/0.2 mixture of sBPDA/BSPA8 or sBPDA (Table 2). These comparative examples use a different diamine and less BSPA8 (Oki’s AN-4-17) than Oki’s Example 11. Oki’s Example 11 composition is more similar to instant Example 4 than Comparative Examples 1-2 because Example 4 uses one of the same diamines and a more similar BSPA8 content. Instant Example 4 is derived from APB-N (Oki’s DI-5-9) and a 0.2/0.8 mixture of sBPDA and BSPA8 and has a dissolution ratio above 90% (Table 1). Instant Example 4 differs from Oki in that Oki uses a 50/50 combination of APB-N and DI-4-1 as the diamine instead of APB-N alone and uses BSPA8 as the only dianhydride instead of a combination of BSPA8 and sBPDA. Instant Examples 1-3 demonstrate that varying the BSPA8 content in the range of 50-100% of the dianhydride results in dissolution ratios above 90% (Table 1). Comparing Examples 2, 4, 9, and 10 demonstrates that the dissolution ratio can be maintained above 90% even as the diamine is changed while holding the BSPA8 content constant. Based on the evidence provided, there is reasonable basis to conclude that the Oki’s polyamic acid varnish is necessarily capable of achieving the claimed dissolution ratio when imidized to form a polyimide film.
Regarding claim 12, Oki discloses the polyamic acid varnish of claim 1.
Oki is silent as to the 5% weight loss temperature (Td5) of a polyimide film prepared from the polyamic acid varnish.
However, the examples in the instant specification demonstrate the properties of polyimide films prepared from polyamic acid varnishes. Of the instant examples, only Comparative Examples 3-6 do not satisfy the claimed Td5. Comparative Examples 3-6 contain diamine components (RT1000, 1000P, D230, or D2000) that are aliphatic polyether amines. Oki’s Example 11 does not contain an aliphatic polyether amine. Oki’s Example 11 composition is more similar to instant Example 4 because Example 4 uses one of the same diamines and a more similar BSPA8 content. Instant Example 4 is derived from APB-N (Oki’s DI-5-9) and a 0.2/0.8 mixture of sBPDA and BSPA8 and has a Td5 of 457 °C (Table 1). Instant Example 4 differs from Oki in that Oki uses a 50/50 combination of APB-N and DI-4-1 as the diamine instead of APB-N alone and uses BSPA8 as the only dianhydride instead of a combination of BSPA8 and sBPDA. Instant Examples 1-3 demonstrate that increasing BSPA8 content from 50 to 100% of the dianhydride component results a Td5 decrease from 477 °C to 460 °C (Table 1). Even Comparative Example 2 that contains no BSPA8 has a Td5 above 500 °C. Examples 2, 4, 9, and 10 hold the BSPA8 content constant, but change the diamine component. These examples have Td5 in the range of 457-464 °C. Based on the evidence provided, there is reasonable basis to conclude that the Oki’s polyamic acid varnish is necessarily capable of achieving the claimed 5% weight loss temperature when imidized to form a polyimide film.
Regarding claim 13, Oki discloses the polyamic acid varnish of claim 1.
Oki is silent as to the elongation percentage of a polyimide film prepared from the polyamic acid varnish.
However, the examples in the instant specification demonstrate the properties of polyimide films prepared from polyamic acid varnishes. Of the instant examples, only Comparative Examples 2 and 5 do not satisfy the claimed elongation ratio (Table 2). These examples have elongation ratios (62% and 58%) slightly below the claimed range (65% or more). Comparative Example 2 is not derived from BSPA8 (Oki’s AN-4-17). Comparative Example 5 is derived from a polyoxypropylene diamine not taught by Oki. Oki’s Example 11 composition is more similar to instant Example 4 than Comparative Examples 2 and 5 because Example 4 uses one of the same diamines and BSPA8. Instant Example 4 is derived from APB-N (Oki’s DI-5-9) and a 0.2/0.8 mixture of sBPDA and BSPA8 and has an elongation ratio of 118% (Table 1). Instant Example 4 differs from Oki in that Oki uses a 50/50 combination of APB-N and DI-4-1 as the diamine instead of APB-N alone and uses BSPA8 as the only dianhydride instead of a combination of BSPA8 and sBPDA. Instant Examples 1-4, 9, and 10 demonstrate that elongation ratios within the claimed range can be achieved when varying the amount of BSPA8 (Examples 1-3) or varying the diamine identity (Examples 2, 4, 9, and 10). These examples have elongation ratios in the range of 73-118%. Based on the evidence provided, there is reasonable basis to conclude that the Oki’s polyamic acid varnish is capable of achieving the claimed elongation ratio when imidized to form a polyimide film.
Regarding claims 15-16, Oki discloses the polyimide composition of claim 14. While not explicitly named an adhesive, the polyimide composition of contains all of the claimed elements and would be expected to be capable of functioning as an adhesive. In addition, the polyimide composition would be expected to be capable of use in a semiconductor component, flexible printed circuit board, coverlay film, or bonding sheet.
Conclusion
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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
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