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 .
Claims 1-21 are pending as amended on 10/18/2023.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-8, in the reply filed on 5/27/2026 is acknowledged.
Claims 9-21 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention, there being no allowable generic or linking claim.
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)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1-8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Miyazaki (EP 3141574; D1 cited on the ISR).
As to claims 1, 2 and 4-8, Miyazaki discloses [0013] a polycarbonate/polyoxyethylene block copolymer comprising a polycarbonate structure (1):
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wherein “R” is pentylene and hexylene [0029-30]. Miyazaki’s formula (1) when R is pentylene and hexylene has a structure according to instant formula (A), wherein instant R is a divalent aliphatic hydrocarbon group and instant R1 is hydrogen. Upon hydrolysis (as recited in instant claims 5 and 6), 1,5-pentanediol and 1,6-hexanediol would be obtained, which would have an average number of carbon atoms between 5 and 6 (within the range recited in instant claim 5). Miyazaki exemplifies block copolymers derived from a polycarbonate diol having a 5.5 average carbon chain length, formed from equimolar amounts of hexanediol and pentanediol (see E1, E2, E4 and E5), which is the same structure and average chain length as the instant polycarbonate diols (P-1, P-5) used to form the block copolymers in instant examples E-1, E-5 and E-6.
Miyazaki’s block copolymer further comprises a polyoxyethylene structure according to formula (2):
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, which corresponds to instant formula (B). Miyazaki exemplifies block copolymers derived from a PEG having a molecular weight of 600 and/or 1000, which is the same as or substantially similar to the molecular weight of the PEG used to form the block copolymers in instant examples E1, E-5 and E-6 (PEG1000) (and which meets instant claims 7 and 8).
Miyazaki discloses that the block copolymer is obtained by transesterification of a polycarbonate diol (3)
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and polyethylene glycol (PEG) (4)
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[0040], which results in the structure derived from the PEG being introduced to any terminal of the polycarbonate diol and the interior of the polycarbonate chain [0065]. When polyoxyethylene structure derived from PEG is introduced to a terminal of a polycarbonate diol via transesterification (as taught by Miyazaki), one terminal oxyethylene unit of the PEG bonds to a carbonyl group via oxygen, resulting in one terminal oxyethylene structure of the PEG becoming a carbonate unit according to instant (BB). When polyoxyethylene structure derived from PEG is introduced to the interior of a polycarbonate chain (as taught by Miyazaki), each of the terminal oxyethylene units of the PEG bond to a carbonyl group via oxygen, resulting in two terminal oxyethylene structures of the PEG becoming carbonate units according to instant (BB).
In Miyazaki’s examples 1, 2, 4 and 5, the mass ratio of polycarbonate diol to PEG is 9 (E1, E4, E5) or 3 (E2), which is the same as the mass ratio used in instant examples E1 and E6 (mass ratio of 9) and instant example E5 (mass ratio of 3). Miyazaki’s block copolymer has a hydroxyl value of 10 to 370 mgKOH [0038], which falls within the presently claimed range of 10-400 mgKOH. The hydroxyl values of each of Miyazaki’s examples 1, 2, 4 and 5 (see Table 1) fall within the presently claimed hydroxy value range, and are substantially similar to the hydroxyl values obtained for instant examples 1, 5 and 6 (see instant Table 2). Relatedly, the number average molecular weights of the block copolymers of Miyazaki’s examples 1, 2, 4 and 5 range from 1013 to 1915 (Table 1), which substantially overlaps the range of number average molecular weights of the copolymers of instant examples 1, 5 and 6 (ranging from 683 to 1317).
As established above, there are substantial similarities between the preparations of the block copolymers exemplified in Miyazaki’s E1, E2, E4 and E5 and the preparations of the copolymers of instant examples E1, E5 and E6 (same chemical structure of polycarbonate diol reactant, same chemical structure of PEG reactant, same or substantially similar PEG reactant molecular weight, same mass ratio of polycarbonate reactant to PEG reactant, same or substantially similar hydroxyl value and molecular weight of final copolymer produced). In the examples, Miyazaki performs the transesterification at substantially the same temperature utilized in the instant examples (150 C in Miyazaki, 145 C in instant examples) for 6 hours and in the presence of a catalyst. Considering the length of Miyazaki’s reaction and the fact that a catalyst is used, there is reasonable basis to conclude that the transesterification reaction resulting in Miyazaki’s copolymers of E1, E2, E4 and E5 progresses to an extent such that the copolymer has a molar quantity of carbonate units corresponding to instant A and oxyethylene units corresponding to instant B within the presently claimed ranges, and, progresses to an extent such that the formation of oxyethylene carbonate units is sufficient to correspond to an instant BB value which results in expression (i) falling within the presently claimed range.
As to claim 3, Miyazaki fails to teach a molecular weight distribution. However, all of the examples in the instant specification (comparative and inventive) have molecular weight distributions within the presently claimed range. As discussed in the rejection above, Miyazaki exemplifies a block copolymer formed by reacting a polycarbonate diol (having the same structure as the exemplified instant polycarbonate diol reactant) with a PEG (having the same structure and the same or substantially similar molecular weight as instant PEG reactants) to form a block copolymer (having substantially the same Mn as instant exemplified copolymers), using transesterification reaction conditions (temperature, catalyst) which are the same as conditions which are exemplified and/or described in the instant specification. Considering that block copolymers having substantially the same chemical structures and molecular weights and formed via substantially the same synthetic procedures must have substantially the same properties, there is reasonable basis to conclude that Miyazaki discloses a block copolymer having a molecular weight distribution which is substantially the same as the molecular weight distribution of the copolymers of the instant examples, i.e., within the presently claimed range.
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(s) 1-8 is/are rejected under 35 U.S.C. 103 as being unpatentable over Miyazaki (EP 3141574; D1 cited on the ISR).
As to claims 1, 2 and 4-8, Miyazaki discloses [0013] a polycarbonate/polyoxyethylene block copolymer comprising a polycarbonate structure (1):
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wherein “R” is preferably 90 mol% or more pentylene and hexylene from a viewpoint that the copolymer tends to be liquid and exhibit water dilutability [0029-30]. Miyazaki’s formula (1) when R is pentylene and hexylene has a structure according to instant formula (A), wherein instant R is a divalent aliphatic hydrocarbon group and instant R1 is hydrogen. Upon hydrolysis (as recited in instant claims 5 and 6), 1,5-pentanediol and 1,6-hexanediol would be obtained, which would have an average number of carbon atoms between 5 and 6 (within the range recited in instant claim 5).
The block copolymer further comprises a polyoxyethylene structure according to formula (2):
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, which corresponds to instant formula (B), and has a hydroxyl value of 10 to 370 mgKOH [0038], which falls within the presently claimed range of 10-400 mgKOH.
Miyazaki discloses that the block copolymer is obtained by transesterification of a polycarbonate diol (3)
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and polyethylene glycol (PEG) (4)
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[0040], which results in the structure derived from the PEG being introduced to any terminal of the polycarbonate diol and the interior of the polycarbonate chain [0065]. When polyoxyethylene structure derived from PEG is introduced to a terminal of a polycarbonate diol via transesterification (as taught by Miyazaki), one terminal oxyethylene unit of the PEG bonds to a carbonyl group via oxygen, resulting in one terminal oxyethylene structure of the PEG becoming a carbonate unit according to instant (BB). When polyoxyethylene structure derived from PEG is introduced to the interior of a polycarbonate chain (as taught by Miyazaki), each of the terminal oxyethylene units of the PEG bond to a carbonyl group via oxygen, resulting in two terminal oxyethylene structures of the PEG becoming carbonate units according to instant (BB). In other words, as transesterification between polycarbonate diol and PEG progresses such that the content of PEG introduced to the interior of chains increases, the content of oxyethylene units bonded to a carbonyl group (units according to instant BB) must increase.
Miyazaki teaches that the mass ratio of polycarbonate structure to polyoxyethylene structure in the block copolymer is preferably 50/50 to 95/5 [0034]. For a polycarbonate structure comprising equal molar amounts pentylene and hexylene units (as used in Miyazaki’s examples, see e.g., [0103]), the mass ratio taught by Miyazaki is equivalent to a molar ratio of polycarbonate to polyoxyethylene of 24/76 ~ 86/14. See table created below for values used to calculate a molar ratio from Miyazaki’s mass ratio:
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A molar ratio of carbonate structural units to oxyethylene structural units of 24/76 to 86/14, as taught by Miyazaki, corresponds to ranges of 24 to 86 mol% carbonate units and 14 to 76 mol% oxyethylene units. There is reasonable basis to conclude, therefore, that Miyazaki’s ranges of carbonate units and oxyethylene units at least substantially overlap the ranges for carbonate (A) units (30 to 90 mol%) and oxyethylene (B) units (10 to 70 mol%) recited in instant claim 1.
Miyazaki fails to specifically teach a value according to instant expression (i).
The value (i) recited in instant claim 1 depends on:
(A) the content of carbonate moieties wherein aliphatic hydrocarbon residues which are not ethylene are attached to carbonate groups (“A” depends on the molecular weight of starting polycarbonate diol, and, on the ratio of polycarbonate diol and PEG reactants),
(B) the content of oxyethylene structural units excluding oxyethylene units which are attached to carbonyls at the terminus of each PEG block (“B” depends on the molecular weight of the PEG reactant, and, on the ratio of polycarbonate diol and PEG reactants);
(BB) the content of oxyethylene units attached to carbonyls of a carbonate group (“BB” increases as the transesterification reaction between polycarbonate diol and PEG progresses, and depends on the number of interior PEG blocks in a polycarbonate chain); and
(Mn) the number average molecular weight of the block polycarbonate/polyoxyethylene copolymer.
Miyazaki discloses the transesterification of PEG and polycarbonate diol using substantially the same conditions (140 to 180 C, normal pressure to 1 MPa [0060-61]; catalyst [0064]) as described in the instant specification (140 to 200 C [0082], normal pressure to 1 MPa [0084], catalyst [0065-70].)
As to instant “A,” Miyazaki teaches [0029-30, 55], and exemplifies, using a polycarbonate diol having the same structure as instant polycarbonate P-1 and P-5 (i.e., from 50/50 pentanediol and hexanediol as polyvalent hydroxy compounds). Miyazaki teaches that the Mn of the polycarbonate diol is preferably 500 to 5000: when greater than 500, expected performance for the block copolymer is further enhanced; when 5000 or less, viscosity is decreased and handleability is enhanced [0056].
As to instant “B,” Miyazaki teaches using PEG having a molecular weight from 400 to 2000: when 400 or more, dispersed particle size decreases and dispersion stability is enhanced, the amount of PEG used can be reduced and heat resistance is enhanced; when 2000 or less, the block copolymer is decreased in crystallinity, is liquid at normal temperature, and enhanced in handleability [0059]. Miyazaki exemplifies using PEG having molecular weight of 600 and/or 1000 (see examples 1 to 8). The range disclosed by Miyazaki falls within the range of 300 to 3000 described in the instant specification in [0052], and recited in instant claim 7.
Additionally relevant to instant “A” and “B,” Miyazaki teaches a mass ratio of polycarbonate to polyoxyethylene structure in [0034] as discussed above, and teaches that above the lower limit of polycarbonate:polyoxyethylene, water resistance and heat resistance are enhanced, while below the upper limit, water dilutability is enhanced [0034]. Like in instant examples E-1 through E-6, Miyazaki exemplifies using polycarbonate diol and PEG in a mass ratio of 9 (see E1, E4, E5) and 3 (see E2).
As to instant “BB,” Miyazaki discloses that disappearance of the peak derived from PEG as a raw material indicates quantitative progression of the transesterification reaction [0104], and transesterification results in the structure derived from the PEG being introduced to any terminal of the polycarbonate diol and the interior of the polycarbonate chain. The peak derived from PEG as a raw material is gradually smaller over time along with progression of the transesterification reaction [0065].
As to instant “Mn,” Miyazaki teaches that the Mn of the block copolymer is more preferably 800 to 3000 in terms of water dilutability. Above a lower limit, expected performance for the composition is further exhibited, while below an upper limit, viscosity increase is suppressed, while handleability and water dilutability is enhanced [0035]. The preferred range for Mn taught by Miyazaki substantially corresponds to the most preferred range for Mn described in the instant specification (1000 to 3200, [0041]).
As set forth above, Miyazaki teaches a block copolymer from the same reactants via substantially the same reaction conditions as described in the instant specification for the preparation of the presently claimed block copolymer. Relevant to variables (A) and (B) in instant expression (i), Miyazaki discloses a range for the content of carbonate units (1) relative to oxyethylene units which substantially overlaps the presently claimed and described ranges, and provides motivation [0034] to select an appropriate ratio of carbonate:oxyethylene in order to achieve a desired balance of water resistance, heat resistance are enhanced, and water dilutability. Miyazaki further provides guidance and motivation to select an appropriate molecular weight for each reactant (polycarbonate diol and PEG) in order to achieve a desired balance between performance, crystallinity, handleability and water dilutability. Relevant to (BB) and (Mn) in instant expression (i), Miyazaki discloses ranges for the molecular weights of the PEG reactant and the final block copolymer which substantially overlap the presently claimed and described ranges, and further provides guidance and motivation to select an appropriate molecular weight for the PEG reactant and final block copolymer in order to achieve a desired balance between performance, handleability and water dilutability.
Given that Miyazaki discloses ratios and molecular weights in ranges which substantially overlap the ranges described in the instant specification for the variables within expression (i), and further given Miyazaki’s disclosure to monitor the transesterification reaction over time until the peak derived from PEG raw material disappears [0065], there is reasonable basis to conclude that Miyazaki suggests copolymers which have a range of values calculated according to instant expression (i) which at least overlaps the presently claimed range of 150 to 400. As discussed, Miyazaki discloses reasons/motivation to increase or decrease values within each of the disclosed ranges in order to achieve a desired balance in properties. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a block copolymer by incorporating the entire amount of PEG raw material into the terminal and interior of a polycarbonate chain by transesterification, as disclosed by Miyazaki, by selecting any ratio of carbonate to oxyethylene units within the range disclosed by Miyazaki, any PEG molecular weight within the range disclosed by Miyazaki, any polycarbonate diol molecular weight within the range disclosed by Miyazaki, and any block copolymer molecular weight within the range disclosed by Miyazaki in order to achieve a desired balance in associated properties, including a ratio and molecular weights which result in a value calculated according to instant expression (i) within the presently claimed range.
As to claim 3, Miyazaki fails to teach a molecular weight distribution. However, all of the examples in the instant specification (comparative and inventive) have molecular weight distributions within the presently claimed range. As discussed in the rejection above, Miyazaki suggests a block copolymer formed by reacting a polycarbonate diol (having the same structure as the instant polycarbonate diol) with a PEG (having the same structure and molecular weight as the instant PEG) to form a block copolymer (having the same Mn as the instant block copolymer), using transesterification reaction conditions (temperature, catalyst) which are the same as conditions described in the instant specification. Considering that block copolymers having substantially the same chemical structures and molecular weights and formed via substantially the same synthetic procedures must have substantially the same properties, there is reasonable basis to conclude that Miyazaki suggests a block copolymer having a molecular weight distribution which is substantially the same as the molecular weight distribution of the copolymers of the instant examples, i.e., within the presently claimed range.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
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/RACHEL KAHN/ Primary Examiner, Art Unit 1766
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