DETAILED ACTION
Election/Restriction
Applicant’s election without traverse of Group I, Claims 1, 2, 4-9 in the reply filed on 03/21/2025 is acknowledged.
Claims 10-19 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim. Election was made without traverse in the reply filed on 03/21/2025.
Response to Amendment
The previous rejections are modified in light of the Applicant’s amendments.
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.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1, 2, 4-9, are 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 1 recites “the polymer of one or more of monoanhydrosugar alcohol and dianhydrosugar alcohol in an amount of 30 to 99% by weight…” However, Claim 1 also recites a “monoanhydrosugar alcohol-alkylene glycol” and “dianhydrosugar alcohol-alkylene glycol” and since a resultant reaction product of an “alkylene glycol” is synonymous/same of an “alkylene oxide” reaction product, it is unclear if the 30-99% of the alkylene oxide adduct polymer of one or more of monoanhydrosugar alcohol and dianhydrosugar alcohol is referring to the wt% amount of the amount of “monoanhydrosugar alcohol-alkylene glycol,” the “dianhydrosugar alcohol-alkylene glycol,” the alkylene-oxide polymer of both the monoanhydrosugar alcohol-alkylene glycol and dianhydrosugar alcohol-alkylene glycol, and/or all of the above.
Claims 2, 4-9, are depending claims which fail to alleviate the issues above.
Claim Rejections - 35 USC § 102
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 1-2, and 5-9, is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by GB 989,144 A to Takeda as cited by the Applicant in IDS dated 11/27/2023. (hereinafter Takeda).
Regarding claims 1-2, and 5-9, Takeda teaches in Example 2, reacting 328 parts sorbitan mixture of 1,4-sorbitan (i.e. monoanhydrosugar alcohol) and 8 wt% of 1,4:3,6-sorbide (i.e. dianhydrosugar alcohol), with 600 parts of propylene oxide (i.e. alkylene oxide) to produce a polyether polyol composition having an average molecular weight of 556 and a hydroxyl number of 404.3 (page 4, ln 40-68), which teaches the claimed anhydrosugar alcohol-alkylene glycol composition of claim 1. The above 1,4-sorbitan has the formula
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138
231
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and the above of 1,4:3,6-sorbide has the formula
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149
169
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, and meets the resultant polymer having claimed formula 1-5 with b and d, and wherein a=0 and c=0.
Takeda also teaches the above reaction mixture (total parts 1000.5), is further heated under reduced pressure to remove the dimethyl sulphoxide and unreacted propylene oxide to obtained 790 parts of the polyether polyol. (page 4, ln 59-64). Before isolation, the reaction mixture thus contains 79 wt% of the polyether polyol. The polyether polyol meets the claimed alkylene oxide (i.e. glycol) adduct polymer of one or more of the monoanhydrosugar and dianhydrosugar alcohols listed above.
In regard to the polydispersity index (PDI), one skilled in the art would have a reasonable expectation for the polyether polyol composition of Takeda to have the claimed PDI properties of the claimed invention because Takeda teaches a substantially identical composition obtained by a substantially identical process such as reacting 328 parts of a mixture of 1,4-sorbitan (i.e. monoanhydrosugar alcohol) and 1,4:3,6-sorbide (i.e. dianhydrosugar alcohol), with 600 parts of propylene oxide, to form a polyether polyol composition, which correlates to 64.7 wt% propylene oxide in the composition which is within the preferred amount of the Applicant’s invention. The Applicant cites in their specification that the addition reaction amount of alkylene oxide to 100 parts by weight of the anhydrosugar alcohol composition is 32 to 400 parts (page 16 of specification), which correlates to 24.2-80 wt% of alkylene oxide in the composition, and further shows from the examples that it is the addition reaction amount of alkylene oxide that gives the composition its claimed properties such as PDI. (See Table 1, Examples, page 15-16, and 28-31), which is further evident by the above polyether polyol composition of Takeda having the claimed molecular weight and hydroxy value. See MPEP 2112.01. (Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977)).
Claim Rejections - 35 USC § 103
The text of those sections of Title 35, U.S. Code not included in this action can be found in a prior Office action.
Claim(s) 4 is/are rejected under 35 U.S.C. 103 as being unpatentable over GB 989,144 A to Takeda as cited by the Applicant in IDS dated 11/27/2023. (hereinafter Takeda).
Regarding claim 4, Takeda teaches the amount of propylene oxide in the reaction mixture is chosen to have a polyether polyol with a hydroxyl number of 350 to 750 (page 2, ln 59-71), which overlaps and meets the claimed properties of claim 4. Takeda further teaches wherein the number of moles of propylene oxide to be reacted with the anhydrohexitol is calculated by the equation
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52
563
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where n=number of hydroxyl groups of anhydrohexitol, M=molecular weight of anhydrohexitol, H-hydroxy number of desired polyether. (page 2, ln 90 to 105). Takeda also teaches the above hydroxyl number range is desired for good physical properties such as stability and compression. (page 2, ln 71-91).
It would have been obvious to one ordinarily skilled in the art before the effective date of the claimed invention to adjust the hydroxy number range of the polyether polyol in the range of 350 to 750 as taught in Takeda by adjusting the amount/moles of propylene oxide using the equation taught in Takeda because Takeda teaches the amount of propylene oxide determines the hydroxy number of the polyether polyol and Takeda also teaches the above hydroxyl number range is desired for good physical properties such as stability and compression. (page 2, ln 59-91).
As cited above, one skilled in the art would have a reasonable expectation for the polyether polyol composition of Takeda to have the claimed PDI, and molecular weight, because Takeda teaches a substantially identical composition obtained by a substantially identical process such as reacting polypropylene oxide with an anhydrohexitol, and that the amount of propylene oxide in the reaction mixture is chosen to have a polyether polyol with a hydroxyl number of 350 to 750 (page 2, ln 59-71), and the Applicant cites in their specification that it is the addition reaction amount of alkylene oxide to the anhydrosugar alcohol composition which determines the claimed properties of the composition such as PDI and molecular weight, (See Table 1, Examples, page 15-16, and 28-31), and this is further evident by the above polyether polyol composition of Takeda having the claimed hydroxy value range and also teaching the amount of propylene oxide determines the properties. See MPEP 2112.01. (Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977)).
Claim(s) 1-2, and 4-9, is/are rejected under 35 U.S.C. 103 as being unpatentable over US 2013/0296451 A1 to Abraham et al. (hereinafter Abraham).
Regarding claims 1, 2, 4-9, Abraham teaches a composition comprising a reaction product of a co-dehydration a sugar alcohol and a reactant polyol (para 3), wherein the reaction product may be alkoxylated by ethylene oxide or propylene oxide (para 46). Specifically, in Example 1, sorbitol is co-dehydrated with glycerol to form a reaction product with 53.49 wt% isosorbide (ISB), 17.47 wt% sorbitan (SBTN), 5.69 wt% glycerin (GLY), and about 8.33 wt% oligomers. (Table 1, para 86-89). Abraham further teaches that above reaction product may be alkoxylated by reacted it with ethylene oxide in an amount of 1-50 wt% of alkylene oxide resulting in a polyol having a hydroxyl number range of 210-400 mg KOH/g (para 46), particularly when low viscosity products such as 10 Pa.s or less are desired. (para 46). The above polyol reaction product meets the claimed alkoxylated-sorbitan, alkoxylated-isosorbide, and alkoxylated-oligomers, and also meets formula 1-5 with b and d, and wherein a=0 and c=0.
It would have been obvious to one ordinarily skilled in the art before the effective date of the claimed invention to alkoxylate the reaction product of Example 1 of Abraham because Abraham teaches that above reaction product may be alkoxylated when a low viscosity product is desired. (para 46).
Using the above teachings, Example 1 correlates to a composition of 73.96 wt% of isosorbide and sorbitan. When Example 1 is alkoxylated by an alkylene oxide (i.e. alkylene glycol), this would result in a polyol composition mixture of alkylene oxide polymers of isosorbide and/or sorbitan, with 73.96 wt% of isosorbide and sorbitan, which meets the claimed wt% amount. Furthermore, the above hydroxy number range of 210-400 mg KOH/g correlates to a hydroxyl equivalent weight (HEW) of 140.25 to 267.1 g/eq, (HEW = 56,100/hydroxyl value), and if the above polyol has a functionality (Fn) of about 3, this correlates to an Mn of 420.75 to 801.3 g/mol, (Mn=Fn x HEW), which overlaps and meets the claimed Mn, hydroxyl equivalent weight, and hydroxy value ranges. (See MPEP 2144.05, “where the claimed ranges ‘overlap or lie inside ranges disclosed by the prior art’ a prima facie case of obviousness exists”).
In regard to PDI, one skilled in the art would have a reasonable expectation for the alkoxylated-polyol composition of Abraham to have the claimed PDI range because Abraham teaches a substantially identical composition obtained by a substantially identical process such as reacting an alkylene oxide with a monoanhydrosugar and diahydrosugar alcohol composition with the claimed wt% amounts, and the Applicant cites in their specification that it is the addition reaction amount of alkylene oxide to the anhydrosugar alcohol composition which determines the claimed properties of the composition such as PDI and molecular weight, (See Table 1, Examples, page 15-16, and 28-31), and this is further evident by the above alkoxylated-polyol composition of Abraham having the claimed hydroxy value range. See MPEP 2112.01. (Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established. In re Best, 562 F.2d 1252, 1255, 195 USPQ 430, 433 (CCPA 1977)).
Response to Arguments
Applicant's arguments filed 07/08/2025 have been fully considered but they are not persuasive.
On page 9-10, the Applicant argues there is no “polymer” of sorbitan or isosorbide. This is not persuasive because, as cited above, Takeda teaches a polyether polyol formed from an addition reaction of propylene oxide with anhydrohexitols (page 1, ln 39-47 and ln 79-81). In example 2, the polyether polyol is obtained by reacting a mixture of 1,4-sorbitan and 1,4:3,6-sorbide (i.e. isosorbide), and propylene oxide. The above sorbitan meets the claimed monoanhydrosugar alcohol, the above isosorbide meets the claimed dianhydrosugar alcohol, and the above polyether polyol of Takeda is a polymer composition of propylene oxide-isosorbide-sorbitan, which correlates and meets the claimed propylene oxide-sorbitan, propylene oxide-isosorbide, and polymer adduct of propylene oxide-isosorbide-sorbitan.
On page 10, the Applicant argues that PDI value is not inherent because Takeda does not teach claimed polymer structure. This is found unpersuasive as addressed above.
On page 10-11, the Applicant argues unexpected good properties. This is not persuasive because the 102 rejection above has been maintained and unexpected results can only overcome 103 obviousness rejections. See MPEP 2131.04, "Evidence of secondary considerations, such as unexpected results or commercial success, is irrelevant to 35 U.S.C. 102 rejections and thus cannot overcome a rejection so based. In re Wiggins, 488 F.2d 538, 543, 179 USPQ 421, 425 (CCPA 1973)."
Furthermore, the Applicant’s evidence of unexpected good properties do not commensurate in scope to the claims which broadly use any alkylene oxide, and broader ranges of Mn, hydroxy value, and/or PDI, while the Applicant’s examples uses propylene oxide or ethylene oxide with a Mn of 317-987, a hydroxyl value of 221-615, and PDI of 1.89-2.58. See MPEP 716.02 (a-e).
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 HA S NGUYEN whose telephone number is (571)270-7395. The examiner can normally be reached Mon-Fri, Flex schedule 7:30am-3:45pm.
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/HA S NGUYEN/Primary Examiner, Art Unit 1766