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 1-20 are pending as filed on 5/27/2022.
Election/Restrictions
Applicant’s election without traverse of Group I, claims 1-9 and 12-20, and species wherein the formed polymer block has the structure (ProDOT-Py-ProDOT)n in the reply filed on 6/23/2025 is acknowledged.
Claims 3, 5, 10, 11, 14 and 16 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected invention or species, there being no allowable generic or linking claim.
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 6, 8, 9, 17, 19 and 20 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.
Claims 6 and 17 refer to and further limits “the reactive functional groups.” Claims 6 and 17 depend from claims 1 and 12, respectively, which recite “at least one reactive functional group connected to each end of the first backbone…” It is not clear whether “the reactive functional groups” recited in claims 6 and 17 refers to the “at least one reactive functional group connected to each end of the first backbone” recited in claim 1 (or claim 12), or, whether “the reactive functional groups” recited in claims 6 and 17 refers to every functional group connected to each end of the first backbone.
Additionally: the scope of claims 8 and 19 is unclear because the meaning of the recited term “benzos” is not clear.
Additionally: Claims 9 and 20 each refer to and further limit “the electron-acceptor group.” However, claims 9 and 20 depend from independent claims 1 and 12, respectively, and neither claim 1 nor claim 12 recites an electron acceptor group. The scope of claims 9 and 20 is therefore unclear due to lack of antecedent basis. Amending claims 9 and 20 to depend from claims 4 and 15, respectively, would resolve the lack of antecedent basis.
However: even if the dependency of claims 9 and 20 were amended to claims 4 and 15, the scope of claims 9 and 20 would remain unclear. Claims 4 and 15 recite “an electron acceptor group” which is sandwiched by two of the electron donor groups. In other words, claims 4 and 15 recite a singular electron acceptor group between two electron donor groups. In contrast, claims 9 and 20 recite that the electron acceptor group comprises a combination of eight different groups. It is unclear how a singular group (as required by claims 4 and 15) could be a combination of all of the groups recited in claims 9 and 20. Applicant may wish to consider amending the claims to utilize Markush language (see formats in MPEP 2173.05(h), e.g., wherein the electron-acceptor group is A, B, or C…), as Applicant likely intended to recite a list of alternatives to define the electron-acceptor group.
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, 2 and 6-8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Bonillo et al (Chain-Growth Polymerization of 2-Chlorothiophenes Promoted by Lewis Acids, J. Am. Chem. Soc. 2012, 134, 18916−18919).
Bonillo discloses the following synthesis and polymerization of a dimer 7 (p 18917) by reacting two electron donor groups (i.e., two Cl-ProDOT monomers):
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, wherein “1” in scheme 3 is “Cl-ProDOT,” which has the following structure:
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.
The dimer “7” in Scheme 3 corresponds to the presently recited “first backbone” because it is formed by the two electron donor groups (i.e., the two ProDOT groups), and, at least one reactive functional group is connected to each end of the first backbone (i.e., H on one end, Cl on the other end, meeting instant claim 6). Therefore, the step of forming a dimer 7 as shown in Bonillo’s Scheme 3 corresponds to the presently recited step of “forming each of reaction units.”
The polymer “8” in Scheme 3 corresponds to the presently recited electrochromic polymer block/second backbone, as it is formed by polymerization of the dimer 7, and is therefore formed by two or more of the dimer 7 structure which corresponds to the presently recited “first backbone.” As to the recitation that the reaction to form the polymer block is “acid-catalyzed cationic polymerization” (and as to instant claim 7) Bonillo teaches that Lewis acids promote the polymerization, and the proposed mechanism is a cationic chain-growth polymerization (abstract).
Bonillo does not characterize the polymer block “8” as “electrochromic,” however, given that the polymer has the same structure as presently recited, there is reasonable basis to conclude that the polymer block is capable of being an “electrochromic” polymer block.
As to claims 2 and 8, Bonillo’s dimer 7 is formed from two Cl-ProDOT monomers which have the same structure (meeting claim 2) and which have a thiophene moiety (meeting instant claim 8).
Claim(s) 1, 2, 4, 6-8, 12, 13, 15 and 17-19 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Beaujuge et al (US 2011/0046330).
Beaujuge discloses that electrochromic polymers (ECPs) have a unique combination of mechanical flexibility, high contrast ratios, and the inherent potential for fine color tunability by control of the structure [0003]. Beaujuge discloses donor-acceptor (DA) conjugated polymers wherein acceptor repeating units are dispersed between a plurality of donor repeating units [0006]. Beaujuge teaches polymerization of a DA-oligomer with at least one interior acceptor repeating unit (and at least one donor repeating unit at both termini of the DA-oligomer) to produce the DA-conjugated polymer [0008].
As to claims 1, 2, 4 and 6-8, Figure 4 of Beaujuge is partially copied below, to show the synthesis of polymers 13a, 13b and 13c:
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Figure 4 copied above shows formation of a DA-oligomer 12 (corresponding to the presently recited reaction units) by reacting two or more of the same thiophene-containing donor groups 10 (corresponding to presently recited two or more electron donor groups), wherein the DA-oligomer 12 includes the backbone formed by the two or more electron donor groups, and has at least one reactive functional group (i.e., H, meeting instant claim 6) connected to each end of the first backbone. With regard to instant claim 4, the (benzothiadiazole) electron acceptor group within DA-oligomer 12 is sandwiched by two of the thiophene-containing donor groups.
Beaujuge discloses a polymerization to form polymer 13 which is catalyzed by FeCl3 (see figure 4 above, reaction of 12 to form 13). FeCl3 is a Lewis acid catalyst (meeting instant claim 7; see instant specification [66]). Beaujuge does not disclose that the polymerization is “cationic,” however, given that Beaujuge discloses reaction of the same monomers as presently recited utilizing the same Lewis acid catalyst as taught in the instant specification, there is reasonable basis to conclude that the polymerization taught by Beaujuge is the same type of polymerization disclosed in the instant claims and specification (cationic). The polymer 13, formed by reacting at least two of the DA-oligomer 12, corresponds to the presently recited electrochromic polymer block.
As to claims 12, 13, 15 and 17-19, Beaujuge discloses a method according to claims 1, 2, 4 and 6-8, as set forth above. Beaujuge further discloses P9, which is a polymer block formed by copolymerization of DA-oligomer 12a with bis-2-ethylhexyloxy substituted ProDOT M8 (see Fig 5A, copied below, as well as [0022-3]):
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As set forth above, formation of a DA-oligomer 12a corresponds to formation of the presently recited reaction units (by reacting two or more of the same thiophene-containing donor groups 10), and the DA-oligomer 12a has a backbone formed by the two or more electron donor groups, and has at least one reactive functional group (i.e., H) connected to each end of the first backbone. The copolymerization of 12a with M8 [0023] corresponds to the presently recited step of forming the electrochromic polymer block (by reacting at least two of the reaction units 12a and M8 with acid catalyzed cationic copolymerization).
Beaujuge further discloses incorporating a film of “P9” into a cell coupled to two electrodes (a silver wire quasi-reference electrode and a platinum wire counter electrode) [0024], and therefore, Beaujuge’s disclosure in [0024] of carrying out electrochemical oxidation of the film using electrolyte and two electrodes corresponds to a method for forming an electrochromic device as presently recited.
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, 2, 4, 6-8, 12, 13, 15 and 17-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Beaujuge et al (US 2011/0046330) in view of Lv et al (Polymeric electrochromic materials with donor–acceptor structures, J. Mater. Chem. C, 2017, 5, 12-28).
(This is a rejection of the presently elected species wherein the polymer block has the structure (ProDOT-Py-ProDOT)n.)
Beaujuge discloses that electrochromic polymers (ECPs) have a unique combination of mechanical flexibility, high contrast ratios, and the inherent potential for fine color tunability by control of the structure [0003]. Beaujuge discloses donor-acceptor (DA) conjugated polymers wherein acceptor repeating units are dispersed between a plurality of donor repeating units [0006]. Beaujuge teaches polymerization of a DA-oligomer with at least one interior acceptor repeating unit (and at least one donor repeating unit at both termini of the DA-oligomer) to produce the DA-conjugated polymer [0008].
As to claims 1, 2, 4 and 6-8, Figure 4 of Beaujuge is partially copied below, to show the synthesis of polymers 13a, 13b and 13c:
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Figure 4 shows formation of a DA-oligomer 12 (corresponding to the presently recited reaction units) by reacting two or more of the same thiophene-containing donor groups 10 (corresponding to the presently recited two or more electron donor groups), wherein the DA-oligomer 12 includes the backbone formed by the two or more electron donor groups, and has at least one reactive functional group (i.e., H, meeting instant claim 6) connected to each end of the first backbone.
Beaujuge discloses a polymerization to form polymer 13 which is catalyzed by FeCl3 (see figure 4 above, reaction of 12 to form 13). FeCl3 is a Lewis acid catalyst (meeting instant claim 7; see instant specification [66]). Beaujuge does not disclose that the polymerization is “cationic,” however, given that Beaujuge discloses reaction of the same monomers as presently recited utilizing the same Lewis acid catalyst as taught in the instant specification, there is reasonable basis to conclude that the polymerization taught by Beaujuge is the same type of polymerization disclosed in the instant claims and specification (cationic). The polymer 13, formed by reacting at least two of the DA-oligomer 12, corresponds to the presently recited electrochromic polymer block.
DA-oligomer 12 contains benzothiadiazole (BTD) as the core electron acceptor group which is sandwiched by two of the thiophene-containing (ProDOT) donor groups. Therefore, the electrochromic polymer block of Beaujuge differs from the presently elected species because the presently elected species has pyridine (Py) as the core electron acceptor group (sandwiched between ProDOT donor groups).
However, Beaujuge teaches that the acceptor unit BTD can be substituted with other acceptor units [0026], and, teaches that electrochromic polymers (ECPs) have the inherent potential for fine color tunability by control of the structure [0003].
Like Beaujuge, Lv teaches that conjugated polymers have gained popularity as a new generation of electrochromic materials due to their diverse colors and fast switching properties (p 12, introduction). Lv teaches that utilization of an appropriate choice of donor (D) and acceptor (A) moieties allows selection of the approximate HOMO and LUMO energies of the resulting polymers, leading to a fine control of the band gap, optical character and electrochromic (EC) properties. Lv teaches that the D unit determines the fundamental color and other EC properties, and conventional D units include thiophene and derivatives thereof (p 13). A large amount of work has been reported on D-A polymers bearing thiophene as D units with tunable colors through the introduction of different electron-acceptor units (p 14, lower left; see also p 20 where Lv discusses the work of Beaujuge). As shown in Table 3 (pp 17-18), in a D-A-D polymer having thiophene-containing (D) groups (EDOT), the color of the polymer when “A” is BTD (see P27) is green (neutral) and transmissive light blue (oxidized), while the color of the polymer when “A” is pyridine (see P19) is red (neutral) and blue-purple (oxidized).
Considering Beaujuge’s disclosure that the BTD acceptor unit can be substituted with other acceptor units, and further considering Lv’s disclosure showing that the colors exhibited by a polymer containing a BTD acceptor unit change upon substitution of the BTD acceptor unit with a pyridine acceptor unit, the person having ordinary skill in the art would have been motivated to substitute the BTD core acceptor unit in Beaujuge’s DA-oligomer 12 for a pyridine acceptor unit, as shown in Table 3 of Lv, in order to vary the accessible colors of the polymer material as desired for an intended application. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out Beaujuge’s synthesis of polymer 13 shown in figure 4 utilizing a DA-oligomer having a structure according to DA-oligomer 12, except wherein the core BTD group has been substituted for a Py group, thereby arriving at a method as presently recited.
As to claims 12, 13, 15 and 17-19, modified Beaujuge suggests a method according to claims 1, 2, 4 and 6-8, as set forth above. Beaujuge further discloses incorporating a film of an electrochromic polymer into a cell coupled to two electrodes (a silver wire quasi-reference electrode and a platinum wire counter electrode) in order to evaluate the properties of the polymer, including the transmittance change upon electro-oxidation and color transition when doped [0024]. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out an electrochemical oxidation of a film as suggested by modified Beaujuge in a cell coupled to two electrodes (corresponding to a method for forming an electrochromic device as presently recited) in order to evaluate the properties of the film.
(Note that if claims 9 and 20 defined the electron-acceptor group as a list of alternatives rather than requiring the inclusion of all recited groups, claims 9 and 20 would have been included in the rejection set forth above.)
Claim(s) 1, 2, 4, 6-8, 12, 13, 15 and 17-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Beaujuge et al (US 2011/0046330) in view of Bonillo et al (Chain-Growth Polymerization of 2-Chlorothiophenes Promoted by Lewis Acids, J. Am. Chem. Soc. 2012, 134, 18916−18919).
The rejection over Beaujuge under 35 USC 102(a)(1) is incorporated here by reference.
Beaujuge discloses a polymerization of thiophene compound 12 to form polymer 13 which is catalyzed by FeCl3 (see figure 4 above, reaction of 12 to form 13). FeCl3 is a Lewis acid catalyst (see instant specification [66]). However, Beaujuge does not disclose that the polymerization is “cationic.”
Bonillo discloses that there is an ongoing need for the development of methodologies for the synthesis of conjugated polymers, particularly polythiophenes, which stand out as one of the most important types of materials (p 18916, left column). Bonillo discloses that Lewis acids promote the polymerization of several 2-chloroalkylenedioxythiophenes via a cationic chain-growth polymerization mechanism, providing high molecular weight polymers (abstract). The living character of Bonillo’s polymerization method enables synthesis of block copolymers (see conclusion on p 18919 and p 18918, right column). The classical cationic methodology makes use of HCl elimination reactions to regain aromatic stability during the polymerization, and Bonillo teaches that the concept can be extended to create other polyaromatic semiconductive polymers (p 18919). Bonillo found that SnCl4 displayed the best performance of Lewis acid catalysts screened, and polymers produced with SnCl4 were more readily neutralized than those produced with other catalysts including FeCl3 (p 18916, right column).
Considering Bonillo’s disclosure, the person having ordinary skill in the art would have been motivated to polymerize thiophene starting compounds via a cationic chain-growth mechanism using SnCl4 as a Lewis acid catalyst in order to achieve good yield and molecular weight performance, and, in order to obtain a polymer that can be readily neutralized. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out Beaujuge’s polymerization of thiophene starting compound (DA-oligomer 12) to form polymer 13 by substituting Beaujuge’s FeCl3-catalyzed polymerization method for Bonillo’s SnCl4-catalyzed cationic polymerization method, thereby arriving at the presently claimed subject matter.
Claim(s) 1, 2, 4, 6-8, 12, 13, 15 and 17-19 is/are rejected under 35 U.S.C. 103 as being unpatentable over Beaujuge et al (US 2011/0046330) in view of Lv et al (Polymeric electrochromic materials with donor–acceptor structures, J. Mater. Chem. C, 2017, 5, 12-28), and further in view of Bonillo et al (Chain-Growth Polymerization of 2-Chlorothiophenes Promoted by Lewis Acids, J. Am. Chem. Soc. 2012, 134, 18916−18919).
The rejection over Beaujuge in view of Lv under 35 USC 103 is incorporated here by reference. As set forth above, modified Beaujuge suggests a method as shown in Beaujuge’s synthesis of polymer 13 shown in figure 4, except wherein the core BTD group of the ProDOT-BTD-ProDOT oligomer 12 has been substituted with a Py group (as taught by Lv). In other words, modified Beaujuge suggests a method of forming an electrochromic block by polymerizing ProDOT-Py-ProDOT, comprising steps according to the instant claims.
Beaujuge discloses polymerization of a D-A-D starting compound (12) which is catalyzed by FeCl3 (see figure 4 above, reaction of 12 to form 13). FeCl3 is a Lewis acid catalyst (see instant specification [66]). However, Beaujuge does not disclose that the polymerization is “cationic.”
Bonillo discloses that there is an ongoing need for the development of methodologies for the synthesis of conjugated polymers, particularly polythiophenes, which stand out as one of the most important types of materials (p 18916, left column). Bonillo discloses that Lewis acids promote the polymerization of several 2-chloroalkylenedioxythiophenes via a cationic chain-growth polymerization mechanism, providing high molecular weight polymers (abstract). The living character of the polymerization method enables synthesis of block copolymers (see conclusion on p 18919 and p 18918, right column). The classical cationic methodology makes use of HCl elimination reactions to regain aromatic stability during the polymerization, and Bonillo teaches that the concept can be extended to create other polyaromatic semiconductive polymers (p 18919). Bonillo found that SnCl4 displayed the best performance of Lewis acid catalysts screened, and polymers produced with SnCl4 were more readily neutralized than those produced with other catalysts including FeCl3 (p 18916, right column).
Considering Bonillo’s disclosure, the person having ordinary skill in the art would have been motivated to polymerize a thiophene-containing starting compound via a cationic chain-growth mechanism using SnCl4 as a Lewis acid catalyst in order to achieve good yield and molecular weight performance, and, in order to obtain a polymer that can be readily neutralized. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out the polymerization of ProDOT-Py-ProDOT, as suggested by modified Beaujuge, by substituting Beaujuge’s FeCl3-catalyzed polymerization method for Bonillo’s SnCl4-catalyzed cationic polymerization method, thereby arriving at the presently claimed subject matter.
Conclusion
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/RACHEL KAHN/ Primary Examiner, Art Unit 1766