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 § 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.
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 1-2, 4-5, 7-8, 10, 12-16, and 18-21 are rejected under 35 U.S.C. 103 as being unpatentable over Yamauchi (WO 2018/186030) in view of Matsui (TWI 776976).
Regarding Claims 1-2, 4-5 and 7-8, Yamauchi discloses a resin composition comprising 100 parts epoxy resin, dicyandiamide, and 3-20 parts core-shell rubber (paras 0008, 0016). The core-shell rubber is in the form of particles (para 0036).
Yamauchi does not disclose the resin composition comprising a compound (C) as claimed.
Matsui discloses matrix resin for prepreg (paras 0013, 0175) where the matrix resin comprises epoxy resin, amine curing agent, and phenolic compound (paras 0017, 0145). The amine curing agent includes dicyandiamide (paras 0133, 0135) and is present in an amount of 5-40% (para 0139) in order to provide suitable viscosity, improve impregnation of the fibers, and improve heat resistance (para 0139). The phenolic compounds include alkyl phenols such as cresol (para 0147) which includes all forms of cresol including where the methyl group is ortho to the hydroxyl group. It is calculated that the MW of cresol is ~ 108 g/mol. The phenolic compounds are present in an amount of 0.01-5% to accelerate the hardening process and improve heat resistance (para 0159).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the present invention to modify Yamauchi to incorporate the teachings of Matsui and produce the resin composition using 5-40% dicyandiamide in order to provide suitable viscosity, improve impregnation of the fibers, and improve heat resistance, and to use 0.1-5% phenolic compounds as disclosed by Matsui to accelerate the hardening process and improve heat resistance.
Although there is no disclosure of the ratio of a number of moles of the phenolic hydroxy group of the phenolic compound to a number of moles of CN groups derived from cyanamide, given that Matsui discloses dicyanamide and phenolic compound identical to that presently claimed, it is clear that the ratio would necessarily meet that presently claimed.
Alternatively, it would have been obvious to one of ordinary skill in the art to use ratio of phenolic compound to dicyandiamide, including ratio a presently claimed, in order to produce composition with desired viscosity, improved impregnation of fibers, desired curing acceleration, and improved heat resistance.
Regarding Claim 10, Yamauchi in view of Matsui discloses all the limitations of the present invention according to Claim 1 above. There is no disclosure in Yamauchi of the ratio of a molar amount of dicyandiamide to a molar amount of epoxy groups of the epoxy resin. However, Yamauchi discloses that the dicyandiamide increases adhesion (para 0028) while the epoxy resin provides good heat resistance (para 0019). Therefore, it would have been obvious to one of ordinary skill in the art to use amount of dicyandiamide and epoxy resin, including ratio as presently claimed, in order to produce composition with both desired adhesion and heat resistance.
Regarding Claim 12-16, Yamauchi in view of Matsui discloses all the limitations of the present invention according to Claim 1 above. Yamauchi further discloses the core-shell rubber particles have core made from butadiene rubber and the shell is made of a plurality of graft chains bonded to the core where the graft chains can include epoxy group (paras 0036-0038). The shell can also be made from PMMA (para 0038).
Regarding Claim 18, Yamauchi in view of Matsui discloses all the limitations of the present invention according to Claim 1 above. Yamauchi further discloses the composition is cured (para 0013).
Regarding Claim 19, Yamauchi in view of Matsui discloses all the limitations of the present invention according to Claim 1 above. Yamauchi further discloses the composition has high adhesion to a substrate (i.e. functions as an adhesive) (para 0017).
Regarding Claim 20, Yamauchi in view of Matsui discloses all the limitations of the present invention according to Claim 19 above. Although there is no disclosure that the composition is a structural adhesive, given that Yamauchi discloses composition identical to that presently claimed, it would necessarily function as a structural adhesive.
Regarding Claim 21, Yamauchi in view of Matsui discloses all the limitations of the present invention according to Claim 19 above. Yamauchi further discloses a metal clad laminate where the composition bonds two metal layers (paras 0055 and 0057).
Claim 9 is rejected under 35 U.S.C. 103 as being unpatentable over Yamauchi in view of Matsui as applied to claim 1 above, and further in view of Masuda et al. (US 2010/0006998 A1).
Regarding Claim 9, Yamauchi in view of Matsui discloses all the limitations of the present invention according to Claim 1 above. Yamauchi in view of Matsui does not disclose a compound (E) as claimed.
Masuda discloses resin composition comprising epoxy resin, and a phenolic hydroxy compound (B) which is a combination of phenolic hydroxy compound (B1) having a molecular weight of 1000 or less and phenolic hydroxy compound (B2) having a molecular weight of 1500 or more and 5000 or less (para 0059), in a weight ratio B1/B2 or 0.1 to 9 (para 0061). The combination provides good tackiness and good adhesive strength (paras 0060-0061). Masuda discloses B1 has two or more phenolic groups and may comprise compounds including bisphenol-A or cresol novolac (para 0062) (i.e. corresponding to the phenolic compound of Matsui). Masuda further discloses B2 has two or more (i.e. including four or more) phenolic hydroxy groups (para 0063).
Therefore it would have been obvious to a person having ordinary skill in the art prior to the filing date of the present invention to modify Yamauchi in view of Matsui to incorporate the teachings of Masuda and produce the resin composition further comprising the phenolic hydroxy compound (B2) of Masuda in a weight ratio of (phenolic compound of Matsui)/( phenolic hydroxy compound (B2) of Masuda) of 0.1 to 9. Doing so would provide good tackiness and good adhesive strength.
Claim 11 is rejected under 35 U.S.C. 103 as being unpatentable over Yamauchi in view of Matsui as applied to claim 1 above, and further in view of Ushiyama et al. (US 2018/0155489).
Regarding Claim 11, Yamauchi in view of Matsui discloses all the limitations of the present invention according to Claim 1 above. Yamauchi further discloses curing accelerator (para 0047) but does not disclose the amount as claimed.
Ushiyama discloses an epoxy composition comprising epoxy resin, dicyandiamide, and imidazole-based curing accelerator (paras 0050-0055). The curing accelerator is present in an amount of 1-30 parts per 100 parts epoxy for sufficient acceleration and superior flame retardancy, heat resistance, and mechanical characteristics (para 0125).
Therefore it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the present invention to modify Yamauchi in view of Matsui to incorporate the teachings of Ushiyama and produce the resin composition using 1-30 parts curing accelerator per 100 parts epoxy. Doing so would produce sufficient acceleration and superior flame retardancy, heat resistance, and mechanical characteristics.
Claim 17 is rejected under 35 U.S.C. 103 as being unpatentable over Yamauchi in view of Matsui as applied to claim 1 above, and further in view of Miyatake (WO 2019/123934).
Regarding Claim 17, Yamauchi in view of Matsui discloses all the limitations of the present invention according to Claim 1 above. Yamauchi further discloses the core-shell rubber particles have shell made of a plurality of graft chains bonded to the core where the graft chains can include epoxy group (paras 0036-0038).
Yamauchi in view of Matsui does not disclose the amount of epoxy groups in the shell layer.
Miyatake discloses epoxy resin composition comprising epoxy resin, epoxy curing agent such as dicyandiamide, and core-shell polymer (paras 0009, 0026). The core-shell polymer includes core made from diene rubber (para 0036) and shell made from polymer grafted to the core (para 0055). The shell polymer is made from monomers including epoxy group containing vinyl monomer in order to stabilize the dispersion of the core-shell polymer in the epoxy resin (paras 0056-0057).
Therefore it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the present invention to modify Yamauchi in view of Matsui to incorporate the teachings of Miyatake and use shell polymer made from monomers including epoxy group containing vinyl monomer. Doing so would stabilize the dispersion of the core-shell polymer in the epoxy resin.
Although there is no disclosure of the amount of epoxy groups in the shell layer as presently claimed, it would have been obvious to one of ordinary skill in the art to use shell with amount of epoxy groups, including that presently claimed, in order to produce a composition where the core-shell is stably dispersed in the epoxy resin.
Claim 1-5, 7-8, 10, 12-16, 18-21, and 23 is rejected under 35 U.S.C. 103 as being unpatentable over Yamauchi in view of Janko (US 2016/0232821 A1) and Matsui.
Regarding Claims 1-5, 7-8, and 23, Yamauchi discloses a resin composition comprising 100 parts epoxy resin, dicyandiamide, and 3-20 parts core-shell rubber (paras 0008, 0016). The core-shell rubber is in the form of particles (para 0036).
Yamauchi does not disclose the resin composition comprising a compound (C) as claimed.
Janko discloses a composition comprising epoxies (Table 2; 0061) and dicyandiamide (para 0045), further comprising 0.1-5% stabilizer such as 4,4′-thiobis(6-tert-butyl-o-cresol) or 2,6-di-tert-butylphenol to provide protection from the effects of thermal and oxidative degradation (para 0108, 0113-0114).
Therefore it would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the present invention to modify Yamauchi to incorporate the teachings of Janko and produce the resin composition of Yamauchi further comprising 0.1-5% stabilizer such as 4,4′-thiobis(6-tert-butyl-o-cresol) or 2,6-di-tert-butylphenol. Doing so would provide protection from the effects of thermal and oxidative degradation.
4,4′-thiobis(6-tert-butyl-o-cresol) has two phenolic hydroxy groups per molecule each with one ortho-positioned substituent as claimed, and has a molecular weight of ~358 g/mol.
2,6-di-tert-butylphenol has one phenolic hydroxy group per molecule with two ortho-positioned substituents as claimed, and has a molecular weight of ~206 g/mol.
Yamauchi in view of Janko does not disclose the molar ratio of the phenolic groups of the stabilizer to the CN groups derived from the dicyandiamide.
Matsui discloses matrix resin for prepreg (paras 0013, 0175) where the matrix resin comprises epoxy resin, amine curing agent, and phenolic compound (paras 0017, 0145). The amine curing agent includes dicyandiamide (paras 0133, 0135) and is present in an amount of 5-40% (para 0139) in order to provide suitable viscosity, improve impregnation of the fibers, and improve heat resistance (para 0139).
It would have been obvious to a person having ordinary skill in the art prior to the effective filing date of the present invention to modify Yamauchi in view of Janko to incorporate the teachings of Matsui and produce the resin composition using 5-40% dicyandiamide. Doing so would provide suitable viscosity, improve impregnation of the fibers, and improve heat resistance.
Although there is no disclosure of the ratio of a number of moles of the phenolic hydroxy group of the phenolic compound to a number of moles of CN groups derived from cyanamide, given that Matsui and Janko discloses dicyanamide and phenolic compound identical to that presently claimed, it is clear that the ratio would necessarily meet that presently claimed.
Alternatively, it would have been obvious to one of ordinary skill in the art to use ratio of phenolic compound to dicyandiamide, including ratio a presently claimed, in order to produce composition with desired viscosity, improved impregnation of fibers, desired curing acceleration, and improved heat resistance.
Regarding Claim 10, Yamauchi in view of Janko and Matsui discloses all the limitations of the present invention according to Claim 1 above. There is no disclosure in Yamauchi of the ratio of a molar amount of dicyandiamide to a molar amount of epoxy groups of the epoxy resin. However, Yamauchi discloses that the dicyandiamide increases adhesion (para 0028) while the epoxy resin provides good heat resistance (para 0019). Therefore, it would have been obvious to one of ordinary skill in the art to use amount of dicyandiamide and epoxy resin, including ratio as presently claimed, in order to produce composition with both desired adhesion and heat resistance.
Regarding Claim 12-16, Yamauchi in view of Janko and Matsui discloses all the limitations of the present invention according to Claim 1 above. Yamauchi further discloses the core-shell rubber particles have core made from butadiene rubber and the shell is made of a plurality of graft chains bonded to the core where the graft chains can include epoxy group (paras 0036-0038). The shell can also be made from PMMA (para 0038).
Regarding Claim 18, Yamauchi in view of Janko and Matsui discloses all the limitations of the present invention according to Claim 1 above. Yamauchi further discloses the composition is cured (para 0013).
Regarding Claim 19, Yamauchi in view of Janko and Matsui discloses all the limitations of the present invention according to Claim 1 above. Yamauchi further discloses the composition has high adhesion to a substrate (i.e. functions as an adhesive) (para 0017).
Regarding Claim 20, Yamauchi in view of Janko and Matsui discloses all the limitations of the present invention according to Claim 19 above. Although there is no disclosure that the composition is a structural adhesive, given that Yamauchi discloses composition identical to that presently claimed, it would necessarily function as a structural adhesive.
Regarding Claim 21, Yamauchi in view of Janko and Matsui discloses all the limitations of the present invention according to Claim 19 above. Yamauchi further discloses a metal clad laminate where the composition bonds two metal layers (paras 0055 and 0057).
Response to Arguments
In light of the amendments filed 03/04/2026, the 35 USC rejection of record of Claim 3 is withdrawn. New grounds of rejection are set forth above.
Applicant's arguments filed 03/04/2026 have been fully considered but they are not persuasive.
Applicant argues that Matsui teaches tertiary amino groups of the formula in para 0147 as the phenolic compounds, not phenols having ortho groups as claimed.
However, while Matsui does teach the tertiary amine phenols as preferable, the fact remains that Matsui does disclose cresol as suitable. Therefore, it would be obvious to use any of the phenols taught by Matsui, including the cresol. Further, applicant has not provided evidence of the criticality of the claimed ortho groups.
Applicant argues that Matsui only discloses motivation for the amount of phenol, but not for the type of phenol.
However, Matsui teaches that amount in reference to the specific types of phenols it discloses. Therefore, a person having ordinary skill in the art would expect the disclosed amount to be in reference to those types. Further, the primary reference Yamauchi does not disclose use of phenol, so Matsui is used to teach the use of phenol (both the type and amount), not to modify an amount of an already disclosed phenol.
Applicant also argues that the claimed molar ratio is critical to achieve desired impact peel performance, pointing to the data of Examples 1-9 and Comparative Examples 2-4 in Table 1.
However, this argument is not persuasive because the data is not commensurate in scope with the scope of the claims. Specifically, the Examples in Table 1 do not use a compound (C) having substituents at ortho positions relative to the phenolic hydroxy group as claimed.
Considering the Examples that do use a compound (C) as claimed (Examples 12, 19-28, and Comparative Example 11), the data is still not commensurate in scope with the scope of the claims. Specifically, the data uses specific epoxy resin, specific blocked urethane, and specific phenolic compounds, while the claims encompass any epoxy resin (A), any core-shell-structured polymer particles or blocked urethane (B), and any compound (C) as claimed. Further, there is no data at the end points of the claimed molar ratios, and Comparative Example 11 has a molar ratio within the claimed range.
Conclusion
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 BETHANY M MILLER whose telephone number is (571)272-2109. The examiner can normally be reached M-F 8:00-4:00.
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/BETHANY M MILLER/Examiner, Art Unit 1787
/CALLIE E SHOSHO/Supervisory Patent Examiner, Art Unit 1787
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