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 .
Claims 1, 98, 100-135 are pending as amended on January 22, 2026. Support for amended claim 1 is found in original claims 1, 99, and 102. Amended claims 100, 101, 107, 108, 110, and 112 are supported by original claims 100, 101, 107, 108, 110, and 112, respectively. New claims 133-135 find support in page 8, line 17 through page 9, line 4 of the specification. Claim 99 is canceled. Claims 115-132 stand withdrawn from consideration.
The new grounds of rejection set forth below were necessitated by Applicant’s amendment incorporating claim 99 and a subset of claim 101 into claim 1 and new claim 135. Therefore, this action is properly made final.
Any objections and/or rejections made in the previous Office action and not repeated below are hereby withdrawn.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 filed January 22, 2026 have been fully considered.
With respect to the rejection of claim 98 under 35 U.S.C. 112(b), Applicant argues (end of page 9) that a skilled person would understand that the claimed “mol/mol ratio of block A to block B” relates to the molar ratio between the number of repeat units in block A and the number of repeat units in block B. The examiner respectfully disagrees that one would understand that claim 98 limits the ratio of the number of repeat units of block A and block B based on the instant disclosure because the mol/mol ratio is not described or demonstrated in the claims or in the instant specification. The rejection has been maintained.
Applicant argues (page 11) that the maximum primary hydroxyl group content achieved by the examples of Hofmann (US 2017/0158804 A1) is 65 mol%. While Hofmann does not exemplify a primary hydroxyl group content >70 mol%, this does not negate a finding of obviousness under 35 USC 103 since a preferred embodiment such as an example is not controlling. Rather, all disclosures “including unpreferred embodiments” must be considered. In re Lamberti 192 USPQ 278, 280 (CCPA 1976) citing In re Mills 176 USPQ 196 (CCPA 1972). Therefore, it would have been obvious to one of ordinary skill in the art to utilize any proportion of primary OH groups in the range of 40-90 mol % given that Hofmann teaches this range (Hofmann, [0110]). A range of 40-90 mol % overlaps with the claimed range of >70 mol %. Selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
Applicant argues (page 12) that Hofmann does not teach a block A with greater than 70% carbonate linkages because Hofmann’s reaction of CO2 and alkylene oxide in step (i) is carried out in the presence of a DMC catalyst which favors the production of ether linkages over carbonate linkages. This argument is not persuasive because Hofmann teaches how to control the distribution of ether and carbonate linkages. In particular, Hofmann teaches that it is possible via the manner and/or sequence of the metered addition of the alkylene oxides and/or the carbon dioxide to synthesize random, alternating, block or gradient polyether carbonate polyols (Hofmann, [0077]). According to Hofmann, it is preferable that an excess of CO2 is used based on the calculated amount of CO2 incorporated into the polyether carbonate polyol (Hofmann, [0082]). In addition, Hofmann teaches that the way in which CO2 is fed depends on how quickly the alkylene oxides are consumed and whether the product is supposed to contain any CO2-free polyether blocks (Hofmann, [0082]).
Applicant’s arguments (page 12-13) regarding Hofmann in view of Moethrath (EP 1359177 A1) are moot because Moethrath is no longer relied upon in the rejection below.
Applicant requests that the double patenting rejection over U.S. Patent No. 12, 351,681 B2 be held in abeyance. This response is incomplete because a complete response to a nonstatutory double patenting (NSDP) rejection is either a reply by applicant showing that the claims subject to the rejection are patentably distinct from the reference claims, or the filing of a terminal disclaimer in accordance with 37 CFR 1.321 in the pending application(s) with a reply to the Office action. See MPEP 804 I (B)(1). NO REJECTION CAN BE HELD IN ABEYANCE.
Claim Objections
Applicant is advised that should claim 111 be found allowable, claim 134 will be objected to under 37 CFR 1.75 as being a substantial duplicate thereof. When two claims in an application are duplicates or else are so close in content that they both cover the same thing, despite a slight difference in wording, it is proper after allowing one claim to object to the other as being a substantial duplicate of the allowed claim. See MPEP § 608.01(m).
Claim Rejections - 35 USC § 112
Claims 98 and 110 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 98 remains rejected because the limitation “the mol/mol ratio of block A to block B is in the range of 25:1 to 1:250” is unclear. It is not clear from either the claims or the specification what is meant by a “mol” of block A or a “mol” of block B and, therefore, one would not know how to calculate whether a block copolymer has a mol/mol ratio within the claimed range.
Claim 110 continues to recited one instance of for example (e.g.). The phrase “(e.g. each Rz is -OH)” (line 15) renders the claim indefinite because it is unclear whether the limitation(s) following the phrase is part of the claimed invention. See MPEP § 2173.05(d).
Claim Rejections - 35 USC § 103
Claims 1, 98, 100-112, 114, and 133-135 are rejected under 35 U.S.C. 103 as being unpatentable over Hofmann (US 2017/0158804 A1).
Regarding claims 1, 100-103, 107, and 114, Hofmann teaches polyether carbonate polyols that are the product of carbon dioxide (CO2) and alkylene oxides added onto a H-functional starter substance ([0012-0021]). Production of the polyether carbonate polyols is broken into steps (i), (ii), and (iii). In step (i), CO2 and a mixture of propylene oxide and at least one further alkylene oxide in a weight ratio of >90:10 are added onto one or more H-functional starter substances ([0013-0016]). Hofmann teaches that the at least one further alkylene oxide can be ethylene oxide ([0044]). In steps (ii) and (iii) the compound is chain extended with propylene oxide and ethylene oxide ([0017-0021]). As described below part of the block produced in step (i) corresponds to instant block A, part of the block produced in step (i) along with the block produced by steps (ii) and (iii) corresponds to instant block B, and the H-functional starter corresponds to the instant starter.
Hofmann does not anticipate proportion of carbonate linkages in block A.
However, Hofmann further teaches that it is possible via the manner and/or sequence of the metered addition of the alkylene oxides and/or the CO2 to synthesize random, alternating, block or gradient polyether carbonate polyols ([0077]). According to Hofmann, it is preferable that an excess of CO2 is used based on the calculated amount of CO2 incorporated into the polyether carbonate polyol ([0082]). In addition, Hofmann teaches that the way in which CO2 is fed depends on how quickly the alkylene oxides are consumed and whether the product is supposed to contain any CO2-free polyether blocks ([0082]). Based on the disclosure of Hofmann, one of ordinary skill would recognize that the relative amounts of ether and carbonate groups could be controlled by controlling the monomer feed. In addition, one would have understood that random, alternating, block or gradient segments could be produced in step (i).
Therefore, it would have been obvious to one of ordinary skill to produce any random, alternating, block or gradient segment derived from CO2 and a >90:10 mixture of propylene oxide and ethylene oxide during step (i) because Hofmann teaches these monomers and monomer arrangements. In particular, it would have been obvious to produce a gradient copolymer from approximately 100% carbonate bonds to approximately 0% carbonate bonds and to have arranged this gradient such that the portion of the segment closest to the starter has mostly carbonate bonds and the portion furthest from the starter has mostly ether bonds.
The starter together with the portions of the step (i) segments closest to the starter where the concentration of carbonate bonds is higher than 80% (claim 101) read on instant block A wherein block A is a polycarbonate block derived from ethylene oxide, propylene oxide, and CO2. Other than the starter, 100% of the residues in block A are derived from alkylene oxides and CO2 (claim 100). Block A has both carbonate and ether bonds (claim 107) and can be considered to be a generally alternating polycarbonate (poly)ol residue (claim 114). The portion of the step (i) segments furthest from the starter where the concentration of carbonate bonds is lower than 80% contribute to the instant B blocks.
The portion of the step (i) segments furthest from the starter where the concentration of carbonate bonds is lower than 80% and the segments derived from steps (ii) and (iii) read on instant block B. Hofmann teaches using propylene oxide and ethylene oxide as alkylene oxides in all three steps ([0017-0021] and [0044]), reading on wherein 100% of the alkylene oxide residues of block B are ethylene or propylene oxide residues (claim 103). In addition to propylene oxide and ethylene oxide, CO2 is used in step (i), reading on wherein block B is a polyethercarbonate block derived from alkylene oxides and CO2 (claim 102).
Hoffman does not anticipate wherein > 70% of the copolymer chain ends are terminated by primary hydroxyl groups.
However, Hofmann teaches a proportion of primary OH groups of 40-90 mol % ([0110]) and further teaches that elevated concentrations of primary end groups impart advantageous isocyanate reactivity ([0191]). It would have been obvious to one of ordinary skill to terminate 40-90 mol% if the copolymer chain ends with primary hydroxyl groups because Hofmann teaches this range. In particular, one would have been motivated to select a terminal hydroxyl content in the upper portion of the prior art range because Hofmann teaches elevated concentrations of primary end groups impart advantageous isocyanate reactivity. A range of 40-90 mol% overlaps with the claimed range of wherein >70% of the copolymer chain ends are terminated by primary hydroxyl groups. 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.
Regarding claims 98 and 105-106, modified Hofmann teaches the (poly)ol block copolymer according to claim 1. For the purposes of examination, the mol/mol ratio of block A to block B is interpreted as a ratio of the number of repeat units in block A and the number of repeat units in block(s) B, consistent with page 9-10 of Applicant’s arguments.
Of the segments produced in step (i), about 60% of each segment is part of block B and about 40% of each segment is part of block A. The relative amounts of block B and block A are estimated using a linear gradient of 100% carbonate bonds to 0% carbonate bonds where block A encompasses the region of 60-100% carbonate bonds (about 80% carbonate bonds overall) and block B encompasses the region of 0-60% carbonate bonds (about 30% carbonate bonds overall). Hofmann further teaches that alkylene oxide blocks produced in step (ii) preferably have 1.5-10 alkylene oxide units ([0100]) and alkylene oxide blocks produced in step (iii) preferably have 1.5-18 alkylene oxide units ([0111]). Steps (ii) and (iii) together produce blocks with 3-28 alkylene oxide units.
Block B as a whole has less than 30% carbonate linkages (claim 105) because the segment from step (i) has about 30% carbonate linkages and the segments from steps (ii) and (iii) have no carbonate linkages. Block B as a whole greater than 70% ether linkages (claim 106) because the segment from step (i) has about 70% ether linkages and the segments from steps (ii) and (iii) have 100% ether linkages.
Step (i) alone suggests a mol/mol ratio of block A to block B of about 2:3 because 40% of the segment produced in step (i) is part of block A. Taken together, steps (i), (ii), and (iii) produce a copolymer where the mol/mol ratio of block A to block B is less than the 2:3 ratio produced in step (i) because steps (ii) and (iii) contribute 3-28 repeat units to each block B. The mol/mol ratio suggested by Hofmann is therefore well within the claimed range of 25:1 to 1:250. For example, even if step (i) only contributed 5 repeat units and steps (ii) and (iii) contributed the maximum of 28 units, the ratio would only increase to about 2:59 (2*28+3=59) when n=1 (claim 98).
Regarding claim 104, modified Hofmann teaches the (poly)ol block copolymer according to claim 1 where the proportion of primary OH groups is 70-90 mol%. Hofmann teaches that the polyether carbonate polyol is chain extended with ethylene oxide ([0020]) and that products having ethylene oxide end blocks are characterized by elevated concentrations of primary end groups which impart advantageous isocyanate reactivity (Hofmann, [0191]). It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have achieved the desired proportion of 70-90 mol% primary OH groups by using approximately 70-90% terminal ethylene oxide residues because Hofmann teaches chain extending the polyol with ethylene oxide and further teaches that such chain extension imparts advantageous isocyanate reactivity.
Regarding claims 108-112 and 133-135, modified Hofmann teaches the (poly)ol block copolymer according to claim 1. As discussed above for claim 1, Hofmann teaches a copolymer where an H-functional starter is extended to form an A block and further extended with B blocks. Hofmann teaches that polyhydric alcohols are suitable as H-functional starters ([0049]). Specific examples of polyhydric alcohols include dihydric alcohols (claim 112) such as ethylene glycol and diethylene glycol (Hofmann, [0049]). These compounds read on wherein the starter compound has the formula Z(Rz)a wherein Z is an alkylene or heteroalkylene, Rz is OH, and a is 2 (claims 110-111 and 133-134). Hofmann further teaches that the H-functional starter substance may also be a polyester polyol (claim 112) consisting of alternating acid and alcohol units (Hofmann, [0051]). This reads on Z is a heteroalkylarylene and a is at least 2 (claims 110-111 and 134-135). Extending the polyhydric H-functional starter substance to from an A block would produce an A block with a Z'-Z-(Z')n starter residue.
The copolymer of Hofmann therefore reads on a (poly)ol block structure of the copolymer is defined as B-A' -Z' -Z-(Z' -A' -B)n wherein n= t-1 and wherein t= the number of terminal OH group residues on the block A; and wherein each A' is independently a polycarbonate chain having at least 80% carbonate linkages.
With respect to the composition of each B block, Hofmann teaches that alkylene oxide blocks produced in step (ii) preferably have 1.5-10 alkylene oxide ([0100]) and alkylene oxide blocks produced in step (iii) preferably have 1.5-18 alkylene oxide units ([0111]). Step (ii) and step (iii) therefore contribute about 3-28 ether linkages. The portion of the gradient copolymer produced in step (i) that contributes to block B has approximately 30% carbonate linkages on average because the gradient of this portion spans about 0% to about 60% carbonate linkages. Block B as a whole has less than 30% carbonate linkages, but more than 1% because the segment from step (i) has about 30% carbonate linkages and the segments from steps (ii) and (iii) have no carbonate linkages. Block B as a whole has greater than 70% ether linkages because the segment from step (i) has about 70% ether linkages and the segments from steps (ii) and (iii) have 100% ether linkages. Hofmann therefore satisfies wherein each B is independently a polyethercarbonate chain having 50-99% ether linkages and at least 1% carbonate linkages (claim 108).
Given that -A’- is derived from ethylene oxide, propylene oxide, and CO2 and comprises >80% carbonate linkages, Hofmann reads on wherein -A'- has the following structure:
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133
282
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wherein the ratio of p:q is at least 8:2 and Re1 and Re2 depend on the nature of the alkylene oxide used to prepare block A.
Similarly, given that block B is derived from ethylene oxide, propylene oxide, and CO2 and has greater than 70% ether linkages, Hofmann reads on wherein block B has the following structure:
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130
302
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wherein the ratio of w:v is greater or equal to about 2.3:1 and Re3 and Re4 depend on the nature of the alkylene oxide used to prepare block B (claim 109).
Claim 113 is rejected under 35 U.S.C. 103 as being unpatentable over Hofmann (US 2017/0158804 A1) as applied to claim 1 above, and further in view of Hofmann (US 2013/0296450 A1, referred to as Hofmann ‘540).
Hofmann teaches the (poly)ol block copolymer according to claim 1. The polyether carbonate polyols of Hoffman are used in flexible polyurethane foams (Hofmann, [0003]). Hofmann teaches that the person skilled in the art is aware that, depending on the respective field of use, the polyether carbonate polyols to be used have to fulfill certain material properties, for example molecular weight (Hofmann, [0173]), but Hofmann is silent as to a specific Mn.
However, Hofmann ‘450 teaches a polyol molecular weight range of 1,800-20,000 Da (Hofmann ‘450, [0086]) for polyether carbonates used in the production of polyurethane flexible foams (Hofmann ‘450, [0107]). It would have been obvious to one of ordinary skill in the art at the time of the invention to form a poly(ol) according to Hofmann having a molecular weight of 1,800-20,000 Da, as Hofmann ‘450 teaches this range as being suitable for similar polyurethane flexible foam precursors. This represents the use of a suitable range of molecular weight in a similar flexible polyurethane foam application. "The combination of familiar elements according to known methods is likely to be obvious when it does no more than yield predictable results." KSR Int'l Co. v. Teleflex Inc., 550 U.S. 398, 416-21 (2007). See MPEP 2141.
Double Patenting
Claims 1, 100-102, 104-112, and 133-135 are rejected on the ground of nonstatutory double patenting as being unpatentable over claim 3 of U.S. Patent No. 12,351,681 B2 (reference application) in view of Hofmann (US 2017/0158804 A1). Although the claims at issue are not identical, they are not patentably distinct from each other because the instant claims are obvious over the reference claim 3 in view of Hofmann.
Regarding claims 1, 100, 102, 104, 107-112, and 133-135, reference claim 3 depends from reference claim 1 and teaches a (poly)ol block copolymer of general structure B-A-(B)n (col. 35, lines 54-59) wherein block A is a polycarbonate chain having at least 70% carbonate linkages (col. 35, lines 63-64), wherein n=t-1 and t=the number of reactive end residues on block A (col. 35, line 61-62), and wherein B is a polyethercarbonate block having 50-90% ether linkages and at least 1% carbonate linkages (col. 35, line 65).
Block A has the structure A’-Z’-Z-(Z’-A’)n (col. 35, line 55) where Z’-Z-(Z’)n is a starter residue selected from alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene, heteroalkynylene, cycloalkylene, cycloalkenylene, heterocycloalkylene, heterocycloalkenylene, arylene, heteroarylene, alkylarylene, heteroalkylarylene, heteroalkylheteroarylene or alkylheteroarylene group or Z may be a combination of any of these groups and Z’ is -O-, -NR’-, -S-, -C(O)O-, -P(O)(OR')O-, PR'(O)(O-)2 or -PR'(O)O- where R’ is selected from H, or optionally substituted alkyl, heteroalkyl, aryl, heteroaryl, cycloalkyl or heterocycloalkyl (col. 36, lines 30-43). The starter residue Z’-Z-(Z’)n reads on a starter residue redrived from a compound that has the formula Z-(Rz)a where instant a corresponds to reference n and instant Rz corresponds to refence Z’. One of ordinary skill would at least envisage n=1, reading on instant a=2 (claims 108, 110-112 and 133-135).
Reference claim 3 teaches that block A has the following structure:
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106
245
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wherein the ratio of p:q is at least 7:3. This block comprises carbonate and ether bonds (claim 107). Reference claim 3 further teaches that block B has the following structure:
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91
272
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wherein the ratio of w:v is greater or equal to 1:1. Re1, Re2, Re3 and Re4 depend on the nature of the epoxide used to prepare blocks A and B (col. 37, lines 3-28). These structures read on those in claim 109 and block A and block B have the same structures as blocks derived from CO2 and alkylene oxides (claims 1, 100, and 102).
Reference claim 3 does not anticipate wherein > 70% of the copolymer chain ends are terminated by primary hydroxyl groups.
However, Hofmann teaches polyether carbonate polyols used in the production of flexible polyurethane foams (Hofmann, [0003]). Hofmann teaches a proportion of primary OH groups of 40-90 mol % (Hofmann, [0110]) and further teaches that products having ethylene oxide end blocks are characterized by elevated concentrations of primary end groups which impart advantageous isocyanate reactivity (Hofmann, [0191]). It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have terminated 40-90 mol% of the chain ends of the polymer of reference claim 3 with ethylene oxide, as taught by Hofmann in order to obtain primary hydroxyl end groups that impart advantageous isocyanate reactivity. A range of 40-90 mol% overlaps with the claimed range of wherein >70% of the copolymer chain ends are terminated by primary hydroxyl groups (claim 1) and wherein at least 70% of the terminal alkylene oxide residues are ethylene oxides residues (claim 104). 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.
Claims 1, 100, 102, 110, and 112 recite product-by-process limitations on the reactants from which the claimed copolymer is derived. It is noted that even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process. See In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985).
To the extent that the process limitations in a product-by-process claim do not carry weight absent a showing of criticality, the reference discloses the claimed product in the sense that the prior art product structure is seen to be no different from that indicated by the claims. The prior art teaches the same product as the instant claims, regardless of the process by which the prior art product has been produced. The burden is shifted to Applicant to provide factually supported evidence which demonstrates the contrary.
Regarding claim 101, reference claim 3 does not anticipate wherein block A has between 80-100% carbonate linkages, however reference claim 3 teaches at least 70% carbonate linkages. It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have selected any carbonate linkage content in the range of 70-100% because reference claim 3 teaches at least 70% carbonate linkages. A range of 70-100% overlaps with the claimed range of 80-100%. 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.
Regarding claims 105-106, reference claim 3 teaches that block B has 50-99% ether linkages and at least 1% carbonate linkages (claim 105) (col. 35, lines 65-67). A range of 50-99% ether linkages overlaps with the claimed range of at least 60% ether linkages (claim 106). 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
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 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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