DETAILED ACTION
The present application, filed on or after March 16, 2013, is being examined under the first inventor to file provisions of the AIA . The amendment filed on 09/08/2026 has been entered. Claims 8 and 9 are cancelled. Claims 1-7 and 10-20 are pending in this application. Claims 1-6 and 14-20 are withdrawn. Claims 7 and 10-13 are currently under examination.
Priority
This application is a 371 of PCT/JP2022/037985 filed on 10/12/2022 and claims foreign priority of JAPAN 2021-173111 filed on 10/22/2021.
Receipt is acknowledged of certified copies of papers required by 37 CFR 1.55.
Should applicant desire to obtain the benefit of foreign priority under 35 U.S.C. 119(a)-(d) prior to declaration of an interference, a certified English translation of the foreign application must be submitted in reply to this action. 37 CFR 41.154(b) and 41.202(e). Failure to provide a certified translation may result in no benefit being accorded for the non-English application.
Election/Restrictions
Applicant's election without traverse of Group III invention (claims 7-13) in the reply filed on 09/08/2026 is acknowledged. Claims 1-6 and 14-20 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected invention or species, there being no allowable generic or linking claim. Thus, claims 7 and 10-13 are currently under examination.
Information Disclosure Statement
Three information disclosure statement (IDS) filed on 04/10/2024, 11/17/2025, and 09/08/2026 have been considered.
Claim Objections
Claims 7 and 12 are objected to because of the following informalities: In claim 7, change the incorrect recitation “represented by” (line 5 of the claim; line 5 on page 4 of 8), which means one of many, to “having”; replace the incorrect recitation “a group selected from” (line 7 of the claim) with “selected from the group consisting of” to comply with Markush group format ending with the conjunction “and” before the last species; insert the missing phrase “to comply with the valency of Si” immediately after the recitation “a is an integer of 0 to 3” (line 11 of the claim); and change the incorrect conjunction “and” (line 3 on page 4 of 8) to “or” because preceding clause recites “selected from” (line 2 on page 4 of 8). In claim 12, change the incorrect recitation “represented by” (line 2), which means one of many, to “having”. Appropriate correction is required.
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 7 and 10-13 are rejected under 35 U.S.C. 103 as being unpatentable over Uchida et al. (US 5,583,244, Dec. 10, 1996, hereinafter referred to as Uchida ‘244, also listed in IDS of 04/10/2024) in view of Keaton et al. (US 9,416.214, Aug. 16, 2016, hereinafter referred to as Keaton ‘214).
With regard to structural limitations “a method comprising steps of subjecting (a) pullulan having a water content of 1.0 mass% or less and a calcium content of less than 100 ppm; and (b) an isocyanate group-containing silicone having the following formula (1):
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, wherein R1 is selected from the group consisting of an alkyl group having 1 to 8 carbon atoms, a cycloalkyl group having 3 to 8 carbon atoms, a fluorine-substituted alkyl group having 1 to 8 carbon atoms, an aryl group having 6 to 12 carbon atoms, and an aralkyl group having 7 to 12 carbon atoms, R2 is an alkyl group having 1 to 4 carbon atoms or a phenyl group, n is an integer of 1 to 10, and a is an integer of 0 to 3, to an addition reaction in the presence of an organometallic compound to thereby obtain the silicone-modified pullulan, wherein the organometallic compound is selected from metal complexes of acetylacetone or a bismuth carboxylate (or the amount of component (b) is 500 to 700 parts by mass, relative to 100 parts by mass of component (a); or conducted in an organic solvent and the amount of the organic solvent is 1,000 to 10,000 parts by mass, relative to 100 parts by mass of component (a))” (claims 7, 10, and 11):
Uchida ‘244 disclosed a siloxane-containing pullulan (
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) prepared by reacting an isocyanato group-containing organosiloxane compound represented by the general formula:
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with at least one glucosic hydroxy group in the molecule of pullulan. Example 2: The isocyanato group-containing organosiloxane compound expressed by the formula:
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is used. Thus, 10g of pullulan having an average molecular weight of about 20,000 after drying at 105° C for 2 hours and 1.2 g of di-n-butyl tin dilaurate were dissolved in 200 ml of N-methyl pyrrolidone at 100° C to form a solution, into which 72.4 g of the above described isocyanato group containing organosiloxane compound were added dropwise under agitation followed by further continued agitation of the reaction mixture for 2 hours at 100 to 110° C and addition of 200 ml of toluene to continue the reaction for 3 hours. After completion of the reaction, the reaction mixture was poured into 1000 ml of methyl alcohol under agitation to precipitate the reaction product which was collected by filtration and washed repeatedly first with methyl alcohol and then with water followed by drying to give 55.2 g of a dried reaction product. The infrared absorption spectrum of this product supports that the product contains a -O-CO-NH-linkage. Pullulan can be prepared biochemically, by culturing a microorganism (col. 1, lines 42-55; col. 2, lines 11-20; col. 5, lines 38-65; col. 6, lines 4-6; col. 3, lines 1-3).
Uchida ‘244 did not explicitly disclose the limitation “the organometallic compound is selected from metal complexes of acetylacetone or a bismuth carboxylate” required by claim 7.
Keaton ‘214 disclosed that Comparative Samples C and D each are the same as Example 7, except the catalyst in each case is 0.25 micromoles of bismuth tris(2-ethylhexanoate). In Sample C, the catalyst is blended with the polyol mixture, and the mixture is then held for about 2 hours at room temperature before adding the polyisocyanate. In Sample D, the catalyst is blended with the polyol mixture, which is then held for about 20 hours at room temperatures before adding the polyisocyanate. Comparative Sample E is the same as Comparative Sample D except 82 mg of a Zeolite are present. Table 3:
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. The bismuth dithiocarbamate catalyst provides a very slow cure in the absence of an activator. Comparative Samples C-E demonstrate the performance of a conventional bismuth carboxylate catalyst. That catalyst cures the mixture even without an activator (Comp. Sample C). Tack-free time is the time after pouring at which the composition no longer sticks to a metal spatula touched to its surface. (page 9/11, col. 16, lines 28-66; page 10/11, col. 17, lines 1-9; page 8/11, col. 14, lines 22-25). Various bismuth compounds have been described as polyurethane catalysts, including bismuth carboxylates. The problems of short pot life can be addressed by using a bismuth catalyst together with certain titanium, Zirconium, hafnium, iron, cobalt or aluminum catalysts. Suitable additional catalysts include, certain chelates of various metals, such as those can be obtained from acetylacetone, benzoylacetone, trifluoroacetyl acetone, or ethyl acetoacetate, with metals such as Be, Mg., Zn, Cd, Pd, Ti, Zr, Al, Sn, As, Bi, Cr, Mo, Mn, Fe, Co and Ni; certain alkaline earth metal, Bi, Pb, Sn or Al carboxylate salts. Various types of isocyanate-reactive materials can be used. One of these is water, which is considered to be an isocyanate reactive material as it consumes two isocyanate groups to produce a urea linkage. Hydroxyl-containing cellulose-lignin materials, hydroxyl containing modified starches as well as the various types of renewable-resource polyols can be used (page 2/11, col. 1, lines 50-63; page 6/11, col. 10, lines 8-24; page 3/11, col. 4, lines 40-43; page 4/11, col. 5, lines 63-65).
Thus, it would have been prima facie obvious to one of ordinary skill in the art at the time the invention was filed to substitute the di-n-butyl tin dilaurate organometallic catalyst as taught by Uchida ‘244 with the bismuth carboxylate with or without additional catalysts including acetylacetone with metals or Bi carboxylate salts in view of Keaton ‘214 to synthesize predominantly polyurethane linkage in water-free organic solvent because (a) the Comparative Sample C (bismuth carboxylate catalyst alone) of Keaton ‘214 requires relatively lower amount of catalyst and no additional activator to achieve comparable tack-free time compared with other catalysts in combination with activator, (b) urea is produced in the presence of water, and (c) pullulan is obtained by microorganism culturing and purification is needed, described above. Thus, one of skill in the art would have a reasonable expectation that by substituting the di-n-butyl tin dilaurate organometallic catalyst as taught by Uchida ‘244 with the bismuth carboxylate with or without additional catalysts including acetylacetone with metals or Bi carboxylate salts in view of Keaton ‘214, followed by optimizing the purity of pullulan and reaction condition, one would achieve Applicant’s claims 7 and 10-13. "Exemplary rationales that may support a conclusion of obviousness include: (B) Simple substitution of one known element for another to obtain predictable results". See MPEP § 2143 [R-01.2024] [I]. "[W]here the general conditions of a claim are disclosed in the prior art, it is not inventive to discover the optimum or workable ranges by routine experimentation." In re Aller, 220 F.2d 454, 456, 105 USPQ 233, 235 (CCPA 1955). See MPEP § 2144.05 [R-01.2024] [II.A].
The method of Uchida ‘244 in view of Keaton ‘214 meets all structural limitation of claimed method and would achieve the same intended results, including “a calcium content of less than 100 ppm and a content of the urea group-containing silicone having the following formula (2) of less than 2,000 ppm”, “an amount of the remaining isocyanate group-containing silicone having the aforesaid formula (1) contained in the silicone-modified pullulan is less than 2,000 ppm”, and “a glass transition point of 100 to 150 ° C as determined by a dynamic viscoelasticity measurement”, required by claims 7, 12, and 13.
Conclusion
No claims are allowed.
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/YIH-HORNG SHIAO/Primary Examiner, Art Unit 1691
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