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 .
Claim Objections
Claims 4 and 5 are objected to because of the following informalities:
Claim 4 recites “at least two reactive hydroxyl, thiol or carboxylic acid groups.” The claim should instead read “at least two reactive hydroxyl, thiol, or carboxylic acid groups.”
Claim 5 recites “at least two reactive hydroxyl, thiol or carboxylic acid groups.” The claim should instead read “at least two reactive hydroxyl, thiol, or carboxylic acid groups.”
Appropriate correction is required.
Claims 26 and 27 are objected to under 37 CFR 1.75(c) as being in improper form because a multiple dependent claim should refer to other claims in the alternative only. See MPEP § 608.01(n). Accordingly, the claims 26 and 27 have not been further treated on the merits.
Claim Analysis
Summary of Claim 1:
An ABA triblock co-polymer comprising:
a first and second A polymer block comprising poly(propylene fumarate); and
a B polymer block comprising a copolymer of a cyclic anhydride and propylene oxide,
wherein said first and second A polymer blocks are each bonded covalently to an end of said B polymer block to form an ABA block copolymer.
Claim Rejections - 35 USC § 103
In the event the determination of the status of the application as subject to AIA 35 U.S.C. 102 and 103 (or as subject to pre-AIA 35 U.S.C. 102 and 103) is incorrect, any correction of the statutory basis (i.e., changing from AIA to pre-AIA ) for the rejection will not be considered a new ground of rejection if the prior art relied upon, and the rationale supporting the rejection, would be the same under either status.
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.
Claims 1-4, 6, 9-14, 17-18, and 25 are rejected under 35 U.S.C. 103 as being unpatentable over Becker et al. (WO 2018142384, hereinafter ‘384) in view of Becker et al. (WO 2020014699, hereinafter ‘699 as listed on IDS dated August 31, 2023).
Regarding claim 1, ‘384 discloses an ABA triblock copolymer comprising ε-decalactone as a B block and maleic anhydride and propylene oxide forming a poly(propylene maleate) block as an A block [00136].
‘384 is silent if the A block of the example is a propylene fumarate as recited in the instant claim.
However, ‘384 teaches that small amount of poly(propylene maleate) adversely affects the ability of the polymer to crosslink. As such, essentially all of the poly(propylene maleate) is converted to poly(propylene fumarate) [0119]. Therefore, it would have been obvious to one of ordinary skill in the art to isomerize the poly(propylene maleate) block to a poly(propylene fumarate) block as taught by ‘384.
‘384 does not disclose the B block is a cyclic anhydride and propylene oxide as recited in the instant claim.
‘699 teaches a poly(propylene fumarate) based copolymer formed from a maleic anhydride, succinic anhydride, and polypropylene shown below:
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forming a poly(propylene maleate propylene succinate) polymer [00101], thereby reading on the B block comprising a cyclic anhydride and propylene oxide of the instant claim. ‘699 offers the motivation that the succinic anhydride reduces the viscosity of the poly(propylene fumarate) and decreases the amount of diethyl fumarate needed to prepare the resin [0062]. ‘384 is also concerned with controlling the viscosity of the polymer and reducing the amount of diethyl fumarate needed to form the resin [0014]. Therefore, one of ordinary skill in art would have found it obvious to substitute the B block of ‘384 with the B block of ‘699 with reasonable expectation that the viscosity of the polymer and the amount of diethyl fumarate needed would be reduced.
Regarding claim 2 and 3, ‘384 is silent on a B block as recited in the instant claims.
However, ‘699 recites a B block comprising succinic anhydride and propylene oxide as shown in the reaction scheme above, thereby reading on the cyclic anhydride of claim 2 and the B polymer block of claim 3. ‘699 offers the motivation that the succinic anhydride reduces the viscosity of the poly(propylene fumarate) and decreases the amount of diethyl fumarate needed to prepare the resin [0062]. ‘384 is also concerned with controlling the viscosity of the polymer and reducing the amount of diethyl fumarate needed to form the resin [0014]. Therefore, one of ordinary skill in art would have found it obvious to substitute the B block of ‘384 with the B block of ‘699 with reasonable expectation that the viscosity of the polymer and the amount of diethyl fumarate needed would be reduced.
Regarding claim 4 and 6, ‘384 discloses an ABA block copolymer formed with 1,4-benzenedimethanol used as an initiator [00136], thereby reading on an initiator having at least 2 reactive hydroxyl groups of instant claim 4 and BDM of instant claim 6.
‘384 is silent on if a residue of the initiator is present in the ABA triblock copolymer as recited in the instant claim.
However, ‘384 teaches the block comprises a polymer chain formed of the residues of the lactones from which it was formed and will be bonded on one end to the residue of the initiating alcohol and on the other end to the poly(propylene fumarate) segment (block) [0075], thereby reading on the residue of an initiator as recited in the instant claim. Therefore, it would have been obvious to one of ordinary skill in the art that ABA triblock copolymer comprises the residue of the initiator as taught by ‘384.
Regarding claim 9, ‘384 in view of 699 teach the ABA block copolymer of claim 1. ‘384 teaches an equimolar quantity of maleic anhydride and propylene oxide were used to form the ABA triblock copolymer [00136]. ‘384 also teaches poly(propylene maleate) can be converted to poly(propylene fumarate) as discussed in the rejection for claim 1 above [0119]. Therefore, the ABA block copolymer comprises 33 mol% of fumarate units and thereby lying within the claimed range.
Regarding claim 10, ‘384 discloses a method of making an ABA triblock copolymer comprising reacting a ε-decalactone, an initiator, and a catalyst to form a B block polymer, then adding maleic anhydride and propylene oxide to react with said B block polymer to form an ABA triblock copolymer [0136], thereby reading on step b).
‘384 does not disclose in step a) a cyclic anhydride and a first quantity of propylene oxide is reacted to form the B block polymer as recited in the instant claim.
‘699 teaches a poly(propylene fumarate) based copolymer formed from a maleic anhydride, succinic anhydride, and polypropylene shown below:
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wherein succinic anhydride, propylene oxide are reacted to form a B block polymer [00101], thereby reading on the cyclic anhydride and propylene oxide of step a) of the instant claim. ‘699 offers the motivation that the succinic anhydride reduces the viscosity of the poly(propylene fumarate) and decreases the amount of diethyl fumarate needed to prepare the resin [0062]. ‘384 is also concerned with controlling the viscosity of the polymer and reducing the amount of diethyl fumarate needed to form the resin [0014]. Therefore, one of ordinary skill in art would have found it obvious to substitute the B block of ‘384 with the B block of ‘699 with reasonable expectation that the viscosity of the polymer and the amount of diethyl fumarate needed would be reduced.
384 is silent if the A block of the example is a propylene fumarate as recited in step c) of the instant claim.
However, ‘384 teaches that small amount of poly(propylene maleate) adversely affects the ability of the polymer to crosslink. As such, essentially all of the poly(propylene maleate) is converted to poly(propylene fumarate) [0119], thereby reading on step c. Therefore, it would have been obvious to one of ordinary skill in the art to isomerize the poly(propylene maleate) block to a poly(propylene fumarate) block as taught by ‘384.
Regarding claims 11 and 12, ‘384 is silent on a B block as recited in the instant claims.
However, ‘699 recites a B block comprising succinic anhydride and propylene oxide as shown in the reaction scheme above, thereby reading on the cyclic anhydride of claim 2 and the B polymer block of claim 3. ‘699 offers the motivation that the succinic anhydride reduces the viscosity of the poly(propylene fumarate) and decreases the amount of diethyl fumarate needed to prepare the resin [0062]. ‘384 is also concerned with controlling the viscosity of the polymer and reducing the amount of diethyl fumarate needed to form the resin [0014]. Therefore, one of ordinary skill in art would have found it obvious to substitute the B block of ‘384 with the B block of ‘699 with reasonable expectation that the viscosity of the polymer and the amount of diethyl fumarate needed would be reduced.
Regarding claim 13, ‘384 discloses a method of making an ABA triblock copolymer comprising reacting a ε-decalactone, an initiator, and a catalyst to form a B block polymer, then adding maleic anhydride and propylene oxide to react with said B block polymer to form an ABA triblock copolymer [0136], thereby reading on step b).
‘384 does not disclose in step a) a succinic anhydride and a first quantity of propylene oxide is reacted to form the B block polymer as recited in the instant claim.
‘699 teaches a poly(propylene fumarate) based copolymer formed from a maleic anhydride, succinic anhydride, and polypropylene shown below:
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wherein succinic anhydride, propylene oxide are reacted to form a B block polymer [00101], thereby reading on the succinic anhydride and propylene oxide of step a) of the instant claim. ‘699 offers the motivation that the succinic anhydride reduces the viscosity of the poly(propylene fumarate) and decreases the amount of diethyl fumarate needed to prepare the resin [0062]. ‘384 is also concerned with controlling the viscosity of the polymer and reducing the amount of diethyl fumarate needed to form the resin [0014]. Therefore, one of ordinary skill in art would have found it obvious to substitute the B block of ‘384 with the B block of ‘699 with reasonable expectation that the viscosity of the polymer and the amount of diethyl fumarate needed would be reduced.
384 is silent if the A block of the example is a propylene fumarate as recited in step c) of the instant claim.
However, ‘384 teaches that small amount of poly(propylene maleate) adversely affects the ability of the polymer to crosslink. As such, essentially all of the poly(propylene maleate) is converted to poly(propylene fumarate) [0119], thereby reading on step c. Therefore, it would have been obvious to one of ordinary skill in the art to isomerize the poly(propylene maleate) block to a poly(propylene fumarate) block as taught by ‘384.
Regarding claim 14, ‘384 is silent on the mole ratio between maleic anhydride to succinic anhydride as recited in the instant claim.
‘699 teaches the mole fraction the maleic anhydride block is about 0.50 to about 0.99 and the mole fraction of succinic anhydride is about 0.01 to about 0.50 [0019], equivalent to a mole ratio of about 0.02 to 2 and thereby overlapping the claimed range. ‘699 offers the motivation that the succinic anhydride reduces the viscosity of the poly(propylene fumarate) and decreases the amount of diethyl fumarate needed to prepare the resin [0062]. ‘384 is also concerned with controlling the viscosity of the polymer and reducing the amount of diethyl fumarate needed to form the resin [0014]. Therefore, one of ordinary skill in art would have found it obvious to modify the ABA triblock copolymer ‘384 with the mole ratio of ‘699 with reasonable expectation that the viscosity of the polymer and the amount of diethyl fumarate needed would be reduced.
Regarding claim 17 and 18, ‘384 discloses an ABA block copolymer formed with 1,4-benzenedimethanol used as an initiator and Mg(BHT)2(THF)2 as the catalyst [00136], thereby reading on the initiator of instant claim 17 and the catalyst of instant claim 18.
Regarding claim 25, ‘384 in view of ‘699 teach the poly(propylene fumarate-b-propylene succinate-b-propylene fumarate) ABA triblock copolymer as rejected in the rejection for claim 13 above.
Claims 7 and 8 are rejected under 35 U.S.C. 103 as being unpatentable over Becker et al. (WO 2018142384, hereinafter ‘384) in view of Becker et al. (WO 2020014699, hereinafter ‘699 as listed on IDS dated August 31, 2023) and in further view of Noro et al. (US 20190077899 as listed on IDS dated August 31, 2023).
The ABA triblock copolymer of claim 1 is incorporated herein by reference.
Regarding claims 7 and 8, ‘384 in view of Becker et al. is silent on the ratio of the degree of polymerization as recited in the instant claim.
Noro et al. teach an ABA triblock copolymer having a ratio of degree of polymerization to a first A polymer block to B polymer block to a second A polymer block is 5-30:90-40:5-30 [0036], equivalent to 1:18:1 to 3:4:3 and thereby overlapping with the claimed range of instant claim 7 and instant claim 8. ‘384 is also concerned with an ABA triblock copolymer. Therefore, it would have been obvious to one of ordinary skill in the art to modify the ABA triblock of ‘384 with ratio of degree of polymerization of Noro et al. because both are related to ABA triblock copolymers and the ratio is well known for ABA triblock copolymers.
Claims 20-23 and 28 are rejected under 35 U.S.C. 103 as being unpatentable over Becker et al. (WO 2018142384, hereinafter ‘384) in view of Becker et al. (WO 2020014699, hereinafter ‘699 as listed on IDS dated August 31, 2023) and Ruckh et al. (US 20200407514 as listed on IDS dated August 31, 2023).
Regarding claim 20, ‘384 discloses an example of an ABA triblock copolymer comprising ε-decalactone as a B block and maleic anhydride and propylene oxide forming a poly(propylene maleate) block as an A block [00136].
‘384 is silent if the A block of the example is a propylene fumarate as recited in the instant claim.
However, ‘384 teaches that small amount of poly(propylene maleate) adversely affects the ability of the polymer to crosslink. As such, essentially all of the poly(propylene maleate) is converted to poly(propylene fumarate) [0119]. Therefore, it would have been obvious to one of ordinary skill in the art to isomerize the poly(propylene maleate) block to a poly(propylene fumarate) block as taught by ‘384.
‘384 does not disclose the B block is propylene succinate as recited in the instant claim.
‘699 teaches a poly(propylene fumarate) based copolymer formed from a maleic anhydride, succinic anhydride, and polypropylene shown below:
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forming a poly(propylene maleate propylene succinate) polymer [00101], thereby reading on propylene succinate of the instant claim. ‘699 offers the motivation that the succinic anhydride reduces the viscosity of the poly(propylene fumarate) and decreases the amount of diethyl fumarate needed to prepare the resin [0062]. ‘384 is also concerned with controlling the viscosity of the polymer and reducing the amount of diethyl fumarate needed to form the resin [0014]. Therefore, one of ordinary skill in art would have found it obvious to substitute the B block of ‘384 with the B block of ‘699 with reasonable expectation that the viscosity of the polymer and the amount of diethyl fumarate needed would be reduced.
‘384 and ‘699 do not disclose a multi-thiol crosslinker as recited in the instant claim.
Ruckh et al. discloses a poly(valerolactone)-co-poly(allylvalerolactone)-co-polyethylene glycol copolymer crosslinked with a dithiol crosslinker by thiolene click chemistry (claim 10, [0212]), thereby reading on a multi-thiol crosslinker having at least two reactive thiol groups. ‘384 also teaches click reactions such as thiol-ene addition reactions can be used to facilitate post polymerization addition of desirable materials to the polymer [0084-0085]. Therefore, it would have been obvious to one of ordinary skill in the art to add the multi-thiol crosslinker of Ruckh et al. with the ABA triblock copolymer of ‘384 in view of ‘699 because dithiols are a well-known crosslinker in the industry.
Regarding claims 21 and 23, ‘384 do not disclose a multi-thiol crosslinker as recited in the instant claim.
Ruckh et al. teach the multi thiol crosslinker is 1,6 hexanedithiol [0012], thereby reading on the multi thiol crosslinker having 2 reactive thiol groups of instant claim 21 and instant claim 23. ‘384 also teaches click reactions such as thiol-ene addition reactions can be used to facilitate post polymerization addition of desirable materials to the polymer [0084-0085]. Therefore, it would have been obvious to one of ordinary skill in the art to add the multi-thiol crosslinker of Ruckh et al. with the ABA triblock copolymer of ‘384 in view of ‘699 because dithiols are a well-known crosslinker in the industry.
Regarding claim 22, ‘384 teaches the block copolymer may be photochemically crosslinked by dissolving the block copolymer diethyl fumarate with conventional photoinitiators [0096], thereby reading on the instant claim.
Regarding claim 28, ‘384 teaches the polymer resin is used as a 3D printable resin [0124], thereby reading on the instant claim.
Allowable Subject Matter
Claims 5, 15-16, 24, and 26-27 are allowed.
Claim 5, 15-16, and 24 are objected to as being dependent upon a rejected base claim, but would be allowable if rewritten in independent form including all of the limitations of the base claim and any intervening claims.
Claims 26 and 27 would be allowable if rewritten or amended to overcome the objection set forth in this Office Action.
The following is a statement of reasons for the indication of allowable subject matter:
Claims 5, 15-16, 24, and 26-27 are allowable over the closest prior art, Becker et al. (WO 201842384, hereinafter ‘384).
Becker et al. disclose a block copolymer comprising a poly(lactone) segment and a poly(propylene fumarate) segment (claim 1).
Becker et al. do not teach or fairly suggest an ABA triblock copolymer having the formula of claim 5 and claim 16 shown below:
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where each n is an integer from about 1 to about 20, each m is an integer from about 2 to about 70, and I is the residue of an initiator having at least two reactive hydroxyl, thiol or carboxylic acid groups,
and the formula of claim 15 as shown below:
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where each n is an integer from about 1 to about 20, each m is an integer from about 2 to about 70, and I is the residue of an initiator having at least two reactive hydroxyl, thiol or carboxylic acid groups.
Regarding claim 24, Becker et al. also do not teach or fairly suggest a ratio of fumarate groups in the ABA triblock copolymer to reactive thiol groups on said multi-thiol crosslinker as recited in the instant claim.
Regarding claims 26 and 27, Becker et al. also do not teach or fairly suggest a method for making the 3D printable polymer resin comprising the specific steps of dissolving the ABA triblock copolymer until the resulting solution has a specific complex viscosity and adding a specific thiol crosslinker.
Conclusion
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/ANDREA WU/Examiner, Art Unit 1763
/JOSEPH S DEL SOLE/Supervisory Patent Examiner, Art Unit 1763
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