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 .
A request for continued examination under 37 CFR 1.114, including the fee set forth in 37 CFR 1.17(e), was filed in this application after final rejection. Since this application is eligible for continued examination under 37 CFR 1.114, and the fee set forth in 37 CFR 1.17(e) has been timely paid, the finality of the previous Office action has been withdrawn pursuant to 37 CFR 1.114. Applicant's submission filed on May 4, 2026 has been entered.
Claims 1, 3-4, 6-8, and 17-19 are pending as amended on May 4, 2026. Support for amended claims 1, 17, 18, and 19 is found in [0043], [0045-0046], [0054-0055], and [0043], respectively. Claim 9 is canceled.
Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn. The text of those sections of Title 35, U.S. Code not included in the action can be found in a prior Office action.
Response to Arguments
Applicant’s arguments, see page 9, filed May 4, 2026, with respect to the rejection(s) of claim(s) 1, 3-4, and 6-9 under 35 U.S.C. 103 have been fully considered and are persuasive. Oswald (US 4,163,832) does not suggest the alicyclic episulfide compound of amended claim 1. Therefore, the rejection has been withdrawn. However, upon further consideration, a new ground(s) of rejection is made in view of Kitayama (JP-2019008289-A).
Claim Objections
Claim 18 is objected to because of the following informalities:
For the utmost clarity, the examiner suggests replacing the chemical structures in claim 18 with higher resolution chemical structures.
For the utmost clarity, the examiner suggests consistent use of superscripts for X3 through X16 when defining the variables in Formulas (2a) and (2-3) through (2-8) in claim 18.
Appropriate correction is required.
Claim Rejections - 35 USC § 103
Claims 1, 3-4, 6-8, and 17-19 are rejected under 35 U.S.C. 103 as being unpatentable over Kitayama (JP-2019008289-A, Cite No. 5 on the 11/16/2022 IDS, references are made to the English translation provided with this Office action).
Regarding claims 1, 4, 6, 8, and 17-19, Kitayama teaches a curable episulfide resin composition comprising an alicyclic episulfide compound and a curing catalyst ([0073]). The curing catalysts taught by Kitayama include 1,8-diazabicyclo [5.4.0] undecane-7 (DBU) ([0085]). DBU reads on a base whose conjugated acid has an acid dissociation constant within the claimed range of 12 or greater (see [0072] of the instant specification). DBU is also an amine compound, reading on claim 4.
The alicyclic episulfide compounds taught by Kitayama include the following compound ([0039]):
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109
232
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. This compound has the same structure as instant formula (1-2) (claim 1) and reads on formula (1-1) where s2 is 1 and s1 is 0 (claim 19).
Kitayama further teaches alicyclic episulfide compounds with the structures shown below ([0050-0051]):
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630
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420
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where the l, m, and n1-n6 are integers of 1-30, R is an alkylene group having 1-8 carbon atoms, and X3-X23 have identical definitions as in instant claim 18 ([0050]). These compounds also satisfy formula (2) in claim 17. For example, formula (2-a) reads on instant Formula (2) where Y is a single bond and X1 and X2 are each independently an oxygen or a sulfur atom, and at least one of X1 and X2 is/are a sulfur atom.
Kitayama further teaches including a thiol as a curing agent ([0097]). The specific thiols suggested by Kitayama include methanedithiol ([0099]) and 3-mercaptopropionic acid ([0102]). It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have included any curing agent taught by Kitayama in the composition, including methanedithiol or 3-mercaptopropionic acid (claim 6). Methanedithiol reads on a thiol compound with two thiol groups (claim 8).
Kitayama teaches that the curable episulfide resin composition is prepared by stirring and mixing the components in a state of being heated as necessary ([0117]). Because no solvent is required in Kitayama’s composition, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have prepared the curable composition without a solvent. Kitayama further teaches that the viscosity of the curable composition at 25 °C is 100-10,000 mPa*s ([0118]). When the viscosity is too low the heat resistance of the cured product decrease, but too high of a viscosity leads to workability problems ([0118]).
After preparing the curable composition, the curable composition is cured to form a cured product ([0119]). As curing conditions, Kitayama teaches temperature range of 10-200 °C, preferably 30-180 °C, and a heating time of 30-60 minutes, preferably 60-480 minutes ([0119]). Kitayama teaches that when the curing temperature is too low, curing is insufficient, but when the curing temperature is too high, decomposition of the resin can occur ([0119]). The cured composition likely has a number average molecular weight (Mn) higher than the claimed range because it is a cured product.
Kitayama does not explicitly teach that a ring-opening polymerization occurs to produce a polythioether compound with a Mn of 500-50,000 prior to the curing process.
However, based on the disclosure of Kitayama, one of ordinary skill would have understood that preparation of the curable composition can include polymerizing the composition components in order to achieve the desired viscosity. In particular, Kitayama teaches that curing occurs in a temperature range of 10-200 °C ([0119]) and also teaches that the curable composition can be prepared by mixing and heating ([0117]). In addition, Kitayama teaches that the viscosity of the curable composition balances heat resistance and workability ([0118]). Given that preparing the curable composition involves heating and mixing to achieve a viscosity in the range of 100-10,000 mPa*s and that the composition is known to cure in a temperature range of 10-200 °C, it is reasonable to expect that the process of preparing the curable composition polymerizes the monomers, reading on performing a ring-opening polymerization of an alicyclic episulfide compound in the presence of a base.
With respect to the Mn of the polythioether, heating the monomers to achieve the desired viscosity range would lead to a Mn range that includes values within the claimed range, as evidenced by the instant specification. Based on the teachings of Kitayama, one of ordinary skill in the art would have understood that increasing the viscosity improves heat resistance and decreasing the viscosity improves workability. One would have further understood that heating the composition leads to polymerization that increases the viscosity of the composition. Therefore, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have optimized the viscosity of Kitayama to any value within the range of 10-10000 mPa*s by heating the composition. One would have been motivated to optimize the viscosity in order to balance heat resistance with workability. The discovery of an optimum value of a known result effective variable, without producing any new or unexpected results, is within the ambit of a person of ordinary skill in the art. See In re Boesch, 205 USPQ 215 (CCPA 1980) (see MPEP § 2144.05, II.). The curable compositions of the instant specification have an identical viscosity range as Kitayama (instant specification, [0134]). These curable compositions comprise polythioethers that have a Mn range of 500-50,000 (instant specification, [0092]) and are prepared from the same alicyclic episulfide compounds as Kitayama (instant specification, [0043], [0045-0046], [0054-0055], and [0043]). The polythioether can be present in the curable composition of the instant specification in an amount of 3 wt.% or greater and less than 100 wt.% (instant specification, [0098]). This suggests that a composition that is close to 100 wt% of a polythioether with a Mn of 500-50,000 will have a viscosity within the range of 100-10,000 mPa*s at 25 °C. Kitayama’s composition with a viscosity optimized within the range 10-10,000 mPa*s at 25 °C therefore necessarily includes polythioethers with a Mn within the claimed range Mn of 500-50,000.
Regarding claim 3, Kitayama teaches the method of claim 1. Kitayama teaches that the curable episulfide resin composition is prepared by stirring and mixing the components in a state of being heated as necessary ([0117]). The mixing temperature of Kitayama reads on in the instant reaction temperature. Kitayama further teaches that the viscosity of the curable composition at 25 °C is 100-10,000 mPa*s in order to balance heat resistance and workability ([0118]). After preparing the curable composition, the curable composition is cured to form a cured product ([0119]). As curing conditions, Kitayama teaches temperature range of 10-200 °C, preferably 30-180 °C, and a heating time of 30-60 minutes, preferably 60-480 minutes ([0119]). Kitayama teaches that when the curing temperature is too low, curing is insufficient, but when the curing temperature is too high, decomposition of the resin can occur ([0119]).
Based on the teachings of Kitayama, one of ordinary skill in the art would have understood that mixing temperature can be used to control viscosity and that polymerization can occur in a temperature range of 10-200 °C. Therefore, it would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have optimized the mixing temperature of Kitayama into a range of 30 °C to 200 °C in order to achieve the target viscosity of 100-10,000 mPa*s at 25 °C. One would have been motivated to optimize the mixing temperature in order to achieve the viscosity required to balance the heat resistance and workability of the curable composition. The discovery of an optimum value of a known result effective variable, without producing any new or unexpected results, is within the ambit of a person of ordinary skill in the art. See In re Boesch, 205 USPQ 215 (CCPA 1980) (see MPEP § 2144.05, II.).
Regarding claim 7, Kitayama teaches the method of claim 6. Kitayama teaches including 0.1-10 parts of the curing catalyst ([0094]) and 30-150 parts of the curing agent ([0110]). Given that Kitayama teaches both monothiols and dithiols as curing agents, this corresponds to a proportion of 0.0003-0.33 equivalents base (curing catalyst) per equivalent of thiol group contained in the thiol compound (curing agent) (10/30=0.33 and 0.1/(150*2)=0.00033).
Kitayama does not anticipate the claimed range of 0.001-1 equivalent base per equivalent of thiol group contained in the thiol compound.
However, it would have been obvious to use any base content in the range of 0.0003-0.33 equivalents base per equivalent of thiol group contained in the thiol compound because Kitayama teaches this range. A range of 0.0003-0.33 overlaps with the claimed range of 0.001-1. It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
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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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
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