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, 4, 11-14 and 21-34 are pending as amended on 10/23/2025.
The new grounds of rejection below were necessitated at least because claim 1 has been amended to recite molecular weight and property limitations which were not previously recited in the examined claims. Therefore, this action is properly made final.
Any rejections and/or objections made in the previous Office action and not repeated below are hereby withdrawn.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 this action can be found in a prior Office Action.
Claim Rejections - 35 USC § 112
The following is a quotation of the first paragraph of 35 U.S.C. 112(a):
(a) IN GENERAL.—The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor or joint inventor of carrying out the invention.
The following is a quotation of the first paragraph of pre-AIA 35 U.S.C. 112:
The specification shall contain a written description of the invention, and of the manner and process of making and using it, in such full, clear, concise, and exact terms as to enable any person skilled in the art to which it pertains, or with which it is most nearly connected, to make and use the same, and shall set forth the best mode contemplated by the inventor of carrying out his invention.
Claim 33 is rejected under 35 U.S.C. 112(a) or 35 U.S.C. 112 (pre-AIA ), first paragraph, as failing to comply with the written description requirement. The claim(s) contains subject matter which was not described in the specification in such a way as to reasonably convey to one skilled in the relevant art that the inventor or a joint inventor, or for applications subject to pre-AIA 35 U.S.C. 112, the inventor(s), at the time the application was filed, had possession of the claimed invention.
Claim 33 has been amended to recite that the catalyst is iron(III) triflate. Paragraph [0054] of the originally filed specification describes Lewis acid catalysts, and includes iron among a list of thirteen elements which can form salts, and further names triflate among a list of three preferred anions which can be used. However, iron triflate is not named anywhere in the specification, iron(III) (i.e., the +3 oxidation state, “ferric”) is not named anywhere in the specification, and none of the Lewis acid catalysts utilized in the twenty six instant examples are an iron salt. Therefore, a method utilizing an iron(III)triflate catalyst was not described in the specification as filed in such a way to reasonably convey to one skilled in the relevant art that the inventor(s) had possession of the claimed invention.
Claim Rejections - 35 USC § 103
Claim(s) 1, 4-14, 21-32 and 34 is/are rejected under 35 U.S.C. 103 as being unpatentable over Luebben et al (US 9040635).
As to claims 1, 13, 26 and 27, Luebben discloses a method of producing a polymer made from glycolaldehyde via the condensation of glycolaldehyde dimer (DHDO) into the polymer thereof (PDHDO) (col 3, lines 37-64). DHDO/glycolaldehyde dimer corresponds to a dimer of alpha-hydroxycarbonyl compound, as recited in claims 1 and 13 (and is 2,5-dihydroxyl-1,4-dioxane, as recited in claim 31). Luebben further teaches several types of useful catalysts, including Lewis acid catalysts (col 7, lines 61-63). See also claim 13 in col 25-26.
Luebben teaches that the dehydration reaction of the dimeric monomer can be carried out by refluxing the monomer and removing the water (col 7, lines 52-55). “A solvent” is taught in the description of the reaction in col 7, line 53, however, Luebben subsequently teaches in col 8, lines 4-5, that “the polymerization can be carried out neat, in a solvent, or a solvent mixture.”
Considering Luebben’s disclosure that the polymerization can be carried out neat or in a solvent, one having ordinary skill in the art would have had a reasonable expectation of success in performing the reaction taught by Luebben by utilizing solvent, or, without addition of any solvent. The person having ordinary skill in the art would have been motivated to omit the use of solvent in order to provide a product with reduced environmental and toxicity concerns. It would have been obvious to the person having ordinary skill in the art, therefore, to have produced a copolymer by condensation polymerization of glycolaldehyde dimer, as taught by Luebben, by carrying out the polymerization neat (i.e., without addition of solvent), as taught by Luebben in col 8, lines 4-5.
Luebben further teaches that in a preferred embodiment, a catalyst is used in combination with one or more water-removal methods, and names the use of dynamic vacuum as an example method (col 8, lines 17-20), which corresponds to the presently recited step of applying vacuum to generate subambient reaction pressure to remove water generated during reaction.
Luebben further teaches a chemical structure wherein “n” (i.e., the number of glycolaldehyde dimer repeating units in the polymer) ranges from 4 to 10,000,000 (col 4, lines 10-26). It is well known in the art that mechanical properties of polymers are linked to polymer molecular weight (e.g., strength and toughness increase as molecular weight increase; as evidence that this is a generally known principle, see Applicant’s Declaration under 37 CFR 1.132 filed 10/23/2025, p 4 (7)). It would have been obvious to the person having ordinary skill in the art, therefore, to have selected any value of “n” within Luebben’s disclosed range in order to achieve a sufficiently high molecular weight which achieves desired mechanical properties for an intended application, including values of “n” corresponding to a weight average molecular weight of 15,000 Da or greater (or, including values of “n” corresponding to a Young’s modulus and/or ultimate tensile strength within the ranges recited in claim 27).
As to claims 12, 21, 28, 30 and 31, Luebben suggests a method according to claims 1 and 27, as set forth above. Luebben fails to provide a general teaching as to a range of suitable reaction temperatures. However, Luebben exemplifies reactions carried out at various temperatures, including 35 C (col 19, line 22) and 50 C (col 20, lines 27 and 43). One having ordinary skill in the art would have had a reasonable expectation that utilizing the temperatures exemplified by Luebben would successfully promote the reaction of the dimer while minimizing degradation of the desired polymer product. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out Luebben’s neat polymerization of glycolaldehyde dimer utilizing similar reaction temperatures to those utilized in Luebben’s examples (e.g., a reaction temperature of 35 C, falling within the range recited in instant claim 12, or, a reaction temperature of 50 C, falling within the ranges recited in instant claims 21 and 30) in order to accelerate the rate of reaction while minimizing degradation of the desired product.
As to claims 4, 22, 23 and 34, Luebben suggests a method according to claims 1, 21 and 30, as set forth above. Luebben teaches using dynamic vacuum in order to remove water (see rejection of claim 3 above). Luebben fails to generally teach a reaction pressure of less than 150 torr. However, one having ordinary skill would have recognized that the purpose of Luebben’s vacuum is to reduce pressure in order to increase the volatility of water and accelerate its removal from the polymer product mixture. It would have been obvious to the person having ordinary skill in the art, therefore, to have applied dynamic vacuum, as taught by Luebben, by increasing the vacuum (decreasing the pressure) to any desired level in order to achieve a desired rate of water removal, including to a level within the presently recited range of less than 150 torr (or less than 30 torr as in claim 22, or 1 torr or less, as in claim 23, or 1-10 torr, as in claim 34).
As to claim 11, Luebben suggests a method according to claims 1 and 4, as set forth above. Luebben teaches removing the water when carrying out the dehydration reaction (col 7, lines 52-55), and teaches dynamic vacuum as an example of a water-removal method (col 8, lines 17-20). When removing water byproduct from a condensation polymerization to drive the reaction/shift equilibrium, the person having ordinary skill in the art would have been motivated to adjust the level of vacuum during the course of the reaction in order to achieve appropriate rates of water removal as the reaction proceeds and polymer molecular weight increases, and, in order to minimize foaming due to water escaping from the reaction/product mixture. It would have been obvious to the person having ordinary skill in the art, therefore, to have produced a copolymer by neat condensation polymerization of glycolaldehyde dimer using dynamic vacuum to remove water, as taught by Luebben, by adjusting and varying the level of the vacuum in order to achieve desired rates of water removal throughout the course of the reaction.
As to claims 14, 25, 29 and 32, Luebben suggests a method according to claims 1, 27 and 30, as set forth above. Luebben teaches that preferred catalysts include metal triflates (col 7, lines 64-66), and claims a method (see claim 13, col 25-26) using a Lewis acid catalyst to promote the dehydration of the monomer (col 25, lines 62-63). Luebben names several Lewis acid salts, including salts of aluminum Al(III), iron Fe(II), and copper Cu(II) (col 26, lines 36-45). With respect to claim 14, Luebben fails to characterize the Lewis acid catalyst as “anhydrous.” However, Luebben teaches that the reactions are run in a glovebox and specifies that the solvents used in the examples are “anhydrous” solvents (see e.g., col 18, lines 3-5). Additionally, as previously discussed, Luebben teaches that the catalyst is used in combination with water-removal methods (col 8, lines 16-20). Considering Luebben’s disclosures, one having ordinary skill in the art would have recognized the importance of minimizing the presence water in order to promote the dehydration taught by Luebben. It would have been obvious to the person having ordinary skill in the art, therefore, to have carried out Luebben’s disclosed polymerization utilizing any Lewis acid catalyst named by Luebben (including a salt, e.g., triflate, of aluminum, iron or copper), and, by using a Lewis acid catalyst which is free of water (anhydrous), in order to promote the dehydration reaction taught by Luebben.
As to claim 24, Luebben suggests a method according to claim 1, as set forth above. As discussed previously, Luebben teaches that the catalyst is used in combination with one or more water removal methods, and names three such methods: Dean-Stark apparatus, use of molecular sieves, or the use of vacuum (col 8, lines 17-20). Considering Luebben’s teaching that one or more methods can be used, it would have been obvious to the person having ordinary skill in the art to have utilized a combination of two or three of any of the three methods named by Luebben in order to remove water from the polymerization reaction, including a combination of vacuum and molecular sieves. Molecular sieves are a dehydrating agent. Therefore, in a method wherein vacuum and molecular sieves are used in combination, as suggested by Luebben, water vapor removed from the reaction by vacuum must contact dehydrating agent as presently recited.
Claim(s) 4, 11, 22, 23 and 34 is/are rejected under 35 U.S.C. 103 as being unpatentable over Luebben et al (US 9040635) in view of Li et al (US 2002/0147368) and Kim et al (US 2014/0142272).
The rejection of claims 1, 21 and 30 over Luebben is incorporated here by reference.
Luebben teaches that in a preferred embodiment, a catalyst is used in combination with one or more water-removal methods, and names the use of dynamic vacuum as an example method (col 8, lines 17-20). However, Luebben fails to exemplify a reaction pressure less than 150 torr (or less than 30 torr, less than 1 torr, or 1-10 torr), and varying the pressure over the course of the reaction.
However, one having ordinary skill in the art would have recognized that in a dehydration reaction, water is produced as an undesired byproduct along with the desired polymer product, and removal of water (such as with the use of dynamic vacuum) drives the reaction toward the product by shifting the equilibrium of the reaction. This concept has been well established, and the selection of appropriate reaction pressure(s) to remove byproduct water would have been within the level of skill in the art. For example, Kim teaches a process of producing a polyester which, like in Luebben’s reaction, requires removal of water byproduct. Kim teaches a pressure of 10 to 100 torr for removing water during a precondensation, and a pressure of 0 to 10 torr for removing water during subsequent polymerization [0005]. As another example, Li teaches applying a 5 torr vacuum to remove water, which shifts the equilibrium toward an acetal product [0032].
Considering the disclosures of Li and Kim, when carrying out a dehydration reaction which requires removal of water from a product mixture using vacuum, it would have been within the level of ordinary skill in the art to select an appropriate level of vacuum (and to appropriately change the level of vacuum as the reaction proceeds), such as vacuum pressures within a range of 0 to 100 torr, in order to accelerate the removal of water byproduct and shift the equilibrium of the dehydration reaction. It would have been obvious to the person having ordinary skill in the art, therefore, to have polymerized glycolaldehyde dimer via a neat dehydration reaction in the presence of Lewis acid catalyst with the application of a dynamic vacuum to remove water, as suggested by Luebben, by selecting any appropriate dynamic vacuum pressure or combination of pressures over the course of the reaction (e.g., within a range of 0 to 100 torr, as taught in Kim and Li) in order to achieve a desired rate of water removal, including pressures within the presently claimed range of less than 150 torr, or less than 30 torr, or 1 torr or less, or 1-10 torr.
Claim(s) 1, 4, 11-14 and 21-33 is/are rejected under 35 U.S.C. 103 as being unpatentable over Peksenar et al (WO 2024/1377152; referred to by second-named inventor in order to distinguish from the rejection over Luebben above).
As to claims 1, 4, 12-14, 21-23 and 25-33, Peksenar discloses a copolymer that comprises two or more glycolaldehyde dimers as monomer units, such as a copolymer comprising 2,5-dihydroxy-1,4-dioxane (DHDO) and 0.1 to 25 wt% monomers other than DHDO (p 2, lines 10-27). 2,5-dihydroxy-1,4-dioxane (as recited in instant claim 31) corresponds to an alpha-hydroxycarbonyl dimer as recited in claims 1 and 27) and a glycolaldehyde dimer as recited in claim 13.
Peksenar discloses polymerization of glycolaldehyde dimers in the presence of a Lewis acid catalyst (corresponding to a Lewis acid catalyst as recited in claim 1) and names Al(OSO2CF3)3, Fe(OSO2CF3)3 and Cu(OSO2CF3)3 (i.e., anhydrous aluminum triflate, anhydrous iron(III) triflate and anhydrous copper triflate salt, meeting instant claims 14, 25, 29, 32 and 33) as examples thereof (p 7, lines 8-20). The polymerization is a condensation polymerization, as evidenced by Peksenar’s disclosure that water or methanol is a byproduct of the reaction (p 7, lines 31-34).
Peksenar teaches that the polymerization can be carried out in a solvent, or in the absence of solvents for its entire duration (p 7, lines 21-30). The person having ordinary skill in the art would have been motivated to omit the use of solvent when feasible in order to provide a product with reduced environmental and toxicity concerns. It would have been obvious to the person having ordinary skill in the art, therefore, to have produced a copolymer by condensation polymerization of glycolaldehyde dimer in the presence of Lewis acid catalyst, as taught by Peksenar, by carrying out the polymerization in the absence of solvents for its entire duration, as taught by Peksenar (corresponding to a polymerization conducted without addition of solvent).
Peksenar further teaches removing byproducts such as water by running the reaction under reduced pressure (p 7, line 31 to p 8, line 1), which corresponds to the instant step of applying vacuum to generate subambient pressure to remove water generated during reaction. Peksenar teaches conducting the reaction under reduced pressure from 4 to 200 mtorr (p 8, lines 6-8). A range of 4 to 200 mtorr (millitorr) is equivalent to 0.004 to 0.2 torr, which falls within the range of less than 150 torr (claim 4), less than 30 torr (claim 22) and 1 torr or less (claim 23).
Peksenar further teaches conducting the reaction at temperatures ranging from 0 to 80 C (p 8, lines 3-6). It would have been obvious to the person having ordinary skill in the art to have utilized any reaction temperature within Peksenar’s disclosed range in order to drive the reaction to completion, including within the presently claimed ranges of 35 to 100 C (claims 12 and 28) or 50-80 C (claims 21 and 30). Case law has established that a prima facie case of obviousness is established where the claimed ranges overlap the ranges disclosed by the prior art. See MPEP 2144.05.
Peksenar further teaches a polymer chemical structure 1 (see p 16) comprising “n” units of “Q,” wherein Q (when R1 and R2 are hydrogen, such as in the preferred embodiment disclosed on p 18, lines 6-7) is DHDO glycolaldehyde dimer. The subscripts in structure 1, including subscripts “n” and “p”, can be integers ranging from zero-10 million (p 16, lines 14-16). It is well known in the art that mechanical properties of polymers are linked to polymer molecular weight (e.g., strength and toughness increase as molecular weight increase; see evidence in Applicant’s Declaration under 37 CFR 1.132 filed 10/23/2025, p 4 (7)). It would have been obvious to the person having ordinary skill in the art, therefore, to have selected any values of subscripts (including “n” and “p”) within Peksenar’s disclosed range in order to achieve a sufficiently high molecular weight which achieves desired mechanical properties for an intended application, including values of “n” and “p” corresponding to a weight average molecular weight of 15,000 Da or greater (or, including values of “n” and “p” corresponding to a Young’s modulus and/or ultimate tensile strength within the ranges recited in claims 1, 27 and 30).
As to claim 11, Peksenar teaches removing byproducts such as water by running the reaction under reduced pressure (p 7, line 31 to p 8, line 1), and, teaches conducting the reaction under reduced pressure from 60 to 120 mtorr (p 8, lines 6-8). One having ordinary skill in the art would have recognized that in a reaction where water is produced as an undesired byproduct, the removal of water (such as with the use of reduced pressure) drives the reaction toward the product by shifting the equilibrium of the reaction. It would have been obvious to the person having ordinary skill in the art, therefore, to have adjusted the pressure of Peksenar’s reaction to any combination of desired pressures within the range of 60 to 120 mtorr over the course of the reaction in order to change or maintain the rate of water removal as appropriate to achieve a desired reaction rate and reaction conversion.
As to claim 24, Peksenar teaches that various methods are used to remove the byproduct (e.g., water) of the reaction, including running the reaction under reduced pressure and the use of dehydrating reagents (p 7, line 31 to p 8, line 2). One having ordinary skill in the art would have recognized that the purpose of removing water in a polycondensation reaction is to drive the reaction to completion, and, therefore, it would have been obvious to the person having ordinary skill in the art to have utilized any one or combination of the methods of removing water taught by Peksenar in order to obtain the desired polymer product, including utilizing a combination of reduced pressure and dehydrating reagents. In a method wherein reduced pressure (vacuum) and dehydrating reagent are used in combination, as suggested by Peksenar, water vapor removed from the reaction by vacuum must contact dehydrating agent as presently recited.
Claim(s) 34 is/are rejected under 35 U.S.C. 103 as being unpatentable over Peksenar et al (WO 2024/1377152) in view of Li et al (US 2002/0147368) and Kim et al (US 2014/0142272).
The rejection of claims 1, 4, 22, 23 and 30 over Peksenar is incorporated here by reference.
Peksenar further teaches removing byproducts such as water by running the reaction under reduced pressure (p 7, line 31 to p 8, line 1), which corresponds to the instant step of applying vacuum to generate subambient pressure to remove water generated during reaction. Peksenar teaches conducting the reaction under reduced pressure from 4 to 200 mtorr (p 8, lines 6-8). A range of 4 to 200 mtorr (millitorr) is equivalent to 0.004 to 0.2 torr, which falls outside the range of 1 to 10 torr recited in claim 34.
However, one having ordinary skill in the art would have recognized that in a dehydration reaction, water is produced as an undesired byproduct along with the desired polymer product, and removal of water drives the reaction toward the product by shifting the equilibrium of the reaction. This concept has been well established, and the selection of appropriate reaction pressure(s) to remove byproduct water would have been within the level of skill in the art. For example, Kim teaches a process of producing a polyester which, like in Peksenar’s reaction, requires removal of water byproduct. Kim teaches a pressure of 10 to 100 torr for removing water during a precondensation, and a pressure of 0 to 10 torr for removing water during subsequent polymerization [0005]. As another example, Li teaches applying a 5 torr vacuum to remove water, which shifts the equilibrium toward an acetal product [0032].
Considering the disclosures of Li and Kim, when carrying out a dehydration reaction which requires removal of water from a product mixture using vacuum, it would have been within the level of ordinary skill in the art to select an appropriate level of vacuum (and to appropriately change the level of vacuum as the reaction proceeds), such as vacuum pressures within a range of 0 to 100 torr, in order to accelerate the removal of water byproduct and shift the equilibrium of the dehydration reaction. It would have been obvious to the person having ordinary skill in the art, therefore, to have polymerized glycolaldehyde dimer via a dehydration reaction in the presence of Lewis acid catalyst with the application of vacuum to remove water, as suggested by Peksenar, by selecting any appropriate vacuum pressure or combination of pressures over the course of the reaction (e.g., within a range of 0 to 100 torr, as taught in Kim and Li) in order to achieve a desired rate of water removal, including pressures within the presently claimed range of 1-10 torr.
Response to Arguments
Applicant's arguments and Declaration filed 10/23/2025 have been fully considered.
Applicant argues (remarks p 7) that WO 2024/137712 (see rejections above over “Peksenar”) is not available as prior art under 35 USC 102(a)(2) because the present application and the PCT application were owned by the same person. This argument is insufficient to overcome the rejections of record over Peksenar for at least the reason that the reference is available as prior art under 35 USC 102(a)(1). The effective filing date of the instant application is April 7, 2025. WO 2024/137712 was published on June 27, 2024. Because Peksenar has a prior public availability date, Peksenar is prior art under 35 USC 102(a)(1). A reference which qualifies as prior art under 35 USC 102(a)(1) cannot be disqualified by a 35 USC 102(b)(2)(C) exception (i.e., commonly owned disclosure exception).
Applicant argues (remarks p 7, Declaration “4”) that Luebben does not teach or suggest that conducting the polymerization in the absence of solvent would give results other than those obtained when the polymerization is carried out in solvent. The examiner agrees that Luebben does not disclose any particular improvement associated with utilizing (or not utilizing) solvent. However, because Applicant has not provided any evidence of unexpected results associated with polymerization in the absence of solvent, this argument fails to overcome the prima facie case of obviousness. Additionally, the fact that the prior art does not contain examples of polymerizations conducted without solvent fails to overcome the rejections of record for at least the reason that anticipatory examples are not requirements of either of 35 USC 102 or 103. The failure of a reference to provide an example of any particular feature described therein neither amounts to a failure of the broader disclosure in the reference to anticipate or suggest the presently claimed subject matter, nor amounts to a teaching away from the disclosure and teachings of the reference. Similarly, disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments (see MPEP 2123).
Applicant further argues (remarks p 7, Declaration “6”) that a reference to Luebben and Raebiger (which is referred to in the cited US patent 9040635 to Luebben) provides data showing polymerizations which result in molecular weights lower than 15,000 as claimed, and, suggests that improved molecular weight can only be achieved using a high boiling solvent or ionic liquid. However, this argument is not sufficient to overcome a rejection of record for at least the reason that the reference to Luebben and Raebiger is not relied on to form a rejection of record.
Applicant further argues (remarks p 8, Declaration “5”) that there is no teaching in Peksenar that polymerization in the absence of solvent would give results other than those obtained when the polymerization is carried out in solvent. The examiner agrees that Peksenar does not disclose any particular improvement associated with utilizing (or not utilizing) solvent. However, because Applicant has not provided any evidence of unexpected results associated with polymerization in the absence of solvent, this argument fails to overcome the prima facie case of obviousness. Additionally, the fact that the prior art does not contain examples of polymerizations conducted without solvent fails to overcome the rejections of record for at least the reason that anticipatory examples are not requirements of either of 35 USC 102 or 103. The failure of a reference to provide an example of any particular feature described therein neither amounts to a failure of the broader disclosure in the reference to anticipate or suggest the presently claimed subject matter, nor amounts to a teaching away from the disclosure and teachings of the reference. Similarly, disclosed examples and preferred embodiments do not constitute a teaching away from a broader disclosure or nonpreferred embodiments (see MPEP 2123).
Applicant argues (remarks p 8, Declaration “5”) that the improved properties described in Peksenar are properties of copolymers including two or more different glycoaldehyde dimers. This argument fails to overcome any rejection of record for at least the reason that the present claims encompass copolymers of glycoaldehyde dimers.
Applicant argues (remarks pp 8-9, Declaration “8”) that two additional polymerization reactions (Exhibit A) demonstrate unexpected increases in molecular weight due to polymerization in the absence of solvent. Applicant’s arguments and evidence provided in the Declaration submitted on 10/23/2025 are insufficient to overcome the rejections of record for at least the following reasons:
Evidence of nonobviousness must be commensurate in scope with the claims which the evidence is offered to support. See MPEP 716.02(d). Therefore, if Applicant wishes to overcome the present rejection by showing unexpected results, Applicant must provide sufficient evidence to show that unexpected results would be obtained for all species encompassed by the present claims. Examples A and B in Exhibit A are solvent-free homopolymerization reactions of DHDO utilizing iron (III) tosylate (0.1 mol% or 0.5 mol%) as the Lewis acid catalyst, with no dehydrating agent, at a temperature of 70 C and at pressure of 1 to 10 torr, for 30 or 60 minutes. In contrast:
many of the instant claims encompass copolymerization reactions and/or do not require DHDO as the monomer compound,
many of the instant claims are not limited to any particular Lewis acid (and none of the instant claims are limited to iron(III)tosylate as the catalyst),
many of the instant claims are not limited to any particular reduced pressure or duration of polymerization,
none of the instant claims exclude the use of dehydrating agents, and
none of the instant claims are limited to a reaction temperature of 70 C.
The results in Exhibit A are therefore not commensurate in scope with the claimed subject matter.
Additionally, the specification as filed contains examples which demonstrate that the absence of solvent is not a critical process parameter for achieving high molecular weight. Of the 26 examples in the instant specification, only examples 14, 21, 22 and 24 are conducted without solvent. Of these four examples, molecular weight is reported only for example 14. The Mw of the polymer produced in example 14 is 3660 Da, which is substantially lower than the polymer products of many of the instant examples carried out in the presence of solvent (see, e.g., polymers of instant examples 3, 6, 7, 10, 11, 18-20 and 23, which have weight average molecular weights ranging from 17,603 to 50,000 Da). The examples in the instant specification, together with Examples A and B in Exhibit A, show that polymerization of glycolaldehyde dimer in the presence of a Lewis acid catalyst at a reduced pressure ranging from 1 to 90 torr and temperatures ranging from 40-70 C results in:
polymers having molecular weights ranging from 2,535 Da to 50,000 when solvent is used (see Examples 2-12, 18-20 and 23) and
polymers having molecular weights ranging from 3,660 to 29,198 when solvent is not used (see Example 14 and Example B).
Because the molecular weight of the exemplified polymers varies over a substantially similar wide range regardless of whether solvent is present or absent, the instant examples contradict Applicant’s assertion that a polymerization conducted in the absence of solvent results in any improvement in Mw or polymer properties (relative to polymerization conducted in the presence of solvent).
Applicant argues (Declaration “8”) that Example A shows an unexpected result: significant retention of elongation at break. This result fails to overcome the rejection of record at least because Example A is not commensurate in scope with any of the claims (for at least the reason that the catalyst used in Example A is iron(III)tosylate; none of the instant claims limit the Lewis acid catalyst to iron(III)tosylate, nor is iron(III)tosylate even described in the specification as filed).
Applicant argues (Declaration “9”) that, according to a 1998 study by Yaylayan (submitted as Exhibit B by Applicant), DHDO degrades in solution over a temperature from 35-85 C, and as a melt at 90 C. However, Applicant has not explained how Yaylayan’s findings would have led one of ordinary skill in the art to expect that, despite a clear teaching in the prior art (i.e., in primary references Luebben and Peksenar) that DHDO can be polymerized neat or in solvent, only polymerization in solvent would be successful. Applicant further argues that it was surprising to find that DHDO and Lewis acid formed a melt at temperatures lower than the nominal melting point of DHDO. However, Applicant has not explained why a mixture of DHDO with Lewis acid would be expected to have the same melting point as pure DHDO.
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.
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/RACHEL KAHN/ Primary Examiner, Art Unit 1766