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 Objections
Claims 5, 8, and 14 are objected to because of the following informalities:
Claim 5, line 2 contains the limitation “one Y radical ortho to the phenol group.” Based on formula (Ib), the examiner suggests that “phenol” should be replaced with “hydroxyl” because the term “phenol” encompasses both the hydroxyl group and the aromatic ring. Alternatively, Applicant may delete “X is H, one Y radical ortho to the phenol group is methoxy, the other two Y radicals are each a radical of the formula (II), and” and “thus.”
In lines 2 of claim 8, the examiner suggests replacing “it” with “the Mannich base” for the utmost clarity of what “it” is.
In the last two lines of claim 14, the examiner suggests deleting the phrase “wherein the curing agent component comprises the curing agent as claimed in claim 10” because it is redundant and does not help clarify the claim.
Appropriate correction is required.
Applicant is advised that should claim 13 be found allowable, claim 14 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
Claim 14 is rejected under 35 U.S.C. 112(b) or 35 U.S.C. 112 (pre-AIA ), second paragraph, as being indefinite for failing to particularly point out and distinctly claim the subject matter which the inventor or a joint inventor (or for applications subject to pre-AIA 35 U.S.C. 112, the applicant), regards as the invention.
Claim 14 recites the limitation "the epoxy resin" in line 1. There is insufficient antecedent basis for this limitation in the claim. This issue can be corrected by replacing “the” with “an” or by making the claim dependent on claim 13.
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)(2) the claimed invention was described in a patent issued under section 151, or in an application for patent published or deemed published under section 122(b), in which the patent or application, as the case may be, names another inventor and was effectively filed before the effective filing date of the claimed invention.
Claims 1-3, 5, 10-11, and 13-15 are rejected under 35 U.S.C. 102(a)(2) as being anticipated by Huber (US 2024/0360271 A1).
The applied reference has a common assignee with the instant application. Based upon the earlier effectively filed date of the reference, it constitutes prior art under 35 U.S.C. 102(a)(2). This rejection under 35 U.S.C. 102(a)(2) might be overcome by: (1) a showing under 37 CFR 1.130(a) that the subject matter disclosed in the reference was obtained directly or indirectly from the inventor or a joint inventor of this application and is thus not prior art in accordance with 35 U.S.C. 102(b)(2)(A); (2) a showing under 37 CFR 1.130(b) of a prior public disclosure under 35 U.S.C. 102(b)(2)(B) if the same invention is not being claimed; or (3) a statement pursuant to 35 U.S.C. 102(b)(2)(C) establishing that, not later than the effective filing date of the claimed invention, the subject matter disclosed in the reference and the claimed invention were either owned by the same person or subject to an obligation of assignment to the same person or subject to a joint research agreement.
Regarding claims 1-3, 5, and 10, Huber discloses amine hardeners for epoxy resins ([0007-0008]). Huber further discloses an amine with the structure shown below (formula (Ij) in [0081]). This compound is a Mannich base and provides for fast curing of epoxy resins ([0068]), reading on a curing agent.
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Huber’s amine reads on a Mannich base of the formula (I) where X is H, one Y radical ortho to the phenol group is methoxy, the other two Y radicals are each a radical of the formula (II), and the Mannich base thus has the formula (Ib) where R1 is H and A is a linear alkylene radical having 2 carbon atoms where the two nitrogen atoms to which the A radical is bonded are separated from one another by two carbon atoms.
Regarding claim 11, Huber discloses a curing agent containing the Mannich base of claim 1. Huber further discloses that the hardener (reading on curing agent) contains at least one further constituent selected from further amines not conforming to Huber’s formula (I), accelerators, and diluents ([0130]). Specific examples of further amines not conforming to Huber’s formula (I) are laid out in [0132-0133] and do not read on instant formula (I).
Regarding claims 13-15, Huber discloses the Mannich base of claim 1. Huber discloses an epoxy resin composition comprising a resin component comprising at least one epoxy resin and a hardener comprising the amine (Mannich base) ([0162-0164]). This reads on an epoxy resin composition comprising a resin component comprising at least one epoxy resin and a curing agent component comprising the Mannich base of claim 1. Huber further discloses an article containing the cured composition ([0211]).
Claim Rejections - 35 USC § 103
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.
Claim 12 is rejected under 35 U.S.C. 103 as being unpatentable over Huber (US 2024/0360271 A1) as applied to claim 11 above.
Huber teaches the curing agent of claim 11. As specific examples of further amines not conforming to Huber’s formula (I), Huber discloses N-furfuryl-1,2-ethanediamine ([0132-0133]).
Hubert lacks sufficient specificity for anticipation of a curing agent further comprising an amine of formula (IV).
However, it would have been obvious to one of ordinary skill to select any further amine taught by Huber, including N-furfuryl-1,2-ethanediamine. N-furfuryl-1,2-ethanediamine reads on formula (IV) where A is an alkylene radical having 2 carbon atoms where the two nitrogen atoms to which the A radical is bonded are separated from one another by two carbon atoms.
Allowable Subject Matter
Claims 4 and 6-9 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
The following is a statement of reasons for the indication of allowable subject matter:
As of the date of this office action, no prior art references, whether considered individually or in combination have been identified to anticipate or render obvious the claimed invention under 35 U.S.C. §102 or §103.
The closest prior art of record is Huber (US 2024/0360271 A1), Kasemi (US 2019/0177472 A1), and Ok (KR 102376268 B1, English translation provided).
As laid out above, Huber discloses a Mannich base with the following structure:
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. This base does not read on formula (Ia) of claim 4 because claim 4’s structure has no methoxy group and no radical of formula (II) para to the OH group. This base does not read on formula (Ic) of claim 6 because claim 6’s structure has three radicals of formula (II). This base does not read on claim 7 because claim 7 requires a dimethylaminomethyl group. One of ordinary skill would not know to make a Mannich base with the structure of claim 4, 6, or 7 based on the disclosure of Huber because Huber’s compounds are derived from vanillin or guaiacol (abstract) and compounds with a hydroxyl group have a methoxy group ortho to the hydroxyl group.
Kasemi teaches curing agents for epoxy resin compositions (abstract). Kasemi teaches the compound shown below ([0063]):
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where a is 0 or 1, b is 0 or 1, and c is 0 or 1 and at least one of a or b or c is 1, and A1 is an alkylene radical with 2-15 carbon atoms which is not 1,2-propylene ([0010] and [0063]). This compound corresponds to formula (I) where X is a linear hydrocarbyl radical having 15 carbon atoms. The number of carbon atoms in A1 overlaps with the number of carbon atoms in A. This compound differs from the instant claims in that there are no furfuryl groups bonded to the primary amines. Kasemi does not fairly suggest modifying the chain ends with furfuryl groups.
Ok teaches a curing agent composition that may be used to cure or crosslink an epoxy resin ([0003]). Ok exemplifies a curing agent with the structure shown below:
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in Example 6 ([0102-0105]). This compound differs from the instant claims in that Ok’s compound has too many NH groups. Based on Ok’s broader disclosure, there must be at least 3 NH groups ([0020] where n is 0) whereas instant formula (II) contains only 2 NH groups.
Claims 4 and 6-7 are allowable. Claims 8-9 depend from claim 6 and are therefore allowable.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AUDRA DESTEFANO whose telephone number is (703)756-1404. The examiner can normally be reached Monday-Friday 9-5.
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If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at (571)272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
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