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 .
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.
Election/Restrictions
Applicant’s election without traverse of the following species in the reply filed on 5/13/2026 is acknowledged.
Monomer of formula CH2=CHC(O)OR) wherein R is a branched (C1-C18) alkyl
Y is -NHRB
CuBr
Claim 13 is withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.
Information Disclosure Statement
The information disclosure statement filed 5/9/2023 fails to comply with 37 CFR 1.98(a)(2), which requires a legible copy of each cited foreign patent document; each non-patent literature publication or that portion which caused it to be listed; and all other information or that portion which caused it to be listed. Applicant did not supply a copy of cited reference to Tasdelen published in Progress In Polymer Science vol. 30 (2011). It has been placed in the application file, but the information referred to therein has not been considered.
Drawings
The drawings are objected to because Fig. 2A contains text within the graphs that is illegible. Corrected drawing sheets in compliance with 37 CFR 1.121(d) are required in reply to the Office action to avoid abandonment of the application. Any amended replacement drawing sheet should include all of the figures appearing on the immediate prior version of the sheet, even if only one figure is being amended. The figure or figure number of an amended drawing should not be labeled as “amended.” If a drawing figure is to be canceled, the appropriate figure must be removed from the replacement sheet, and where necessary, the remaining figures must be renumbered and appropriate changes made to the brief description of the several views of the drawings for consistency. Additional replacement sheets may be necessary to show the renumbering of the remaining figures. Each drawing sheet submitted after the filing date of an application must be labeled in the top margin as either “Replacement Sheet” or “New Sheet” pursuant to 37 CFR 1.121(d). If the changes are not accepted by the examiner, the applicant will be notified and informed of any required corrective action in the next Office action. The objection to the drawings will not be held in abeyance.
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.
The following is a quotation of 35 U.S.C. 112(d):
(d) REFERENCE IN DEPENDENT FORMS.—Subject to subsection (e), a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
The following is a quotation of pre-AIA 35 U.S.C. 112, fourth paragraph:
Subject to the following paragraph [i.e., the fifth paragraph of pre-AIA 35 U.S.C. 112], a claim in dependent form shall contain a reference to a claim previously set forth and then specify a further limitation of the subject matter claimed. A claim in dependent form shall be construed to incorporate by reference all the limitations of the claim to which it refers.
Claim 9 is 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.
Regarding claim 9: Claim 9 states that the polyolefin comprises “monomers derived from ethylene”. It is unclear whether this phrase is intended to require that a derivative of ethylene (e.g., vinyl chloride) is used as a monomer for the production of the polyolefin block, or if the phrase “derived from” is intended to refer to polymerized units of ethylene.
Claim 2 is rejected under 35 U.S.C. 112(d) or pre-AIA 35 U.S.C. 112, 4th paragraph, as being of improper dependent form for failing to further limit the subject matter of the claim upon which it depends, or for failing to include all the limitations of the claim upon which it depends.
Claim 2 depends from claim 1, and states that the CH2=CH-(X) monomers may comprise glycidyl acrylate. Glycidyl acrylate has the structure shown below.
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128
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Note, however, that independent claim 1 defines the variable X in the formula CH2=CH-(X) as being -C(O)OR, -CN, or C(O)NHR wherein R is chosen from -H, linear (C1-C18) alkyl, or branched (C1-C18) alkyl. As glycidyl acrylate contains an epoxide group, it does not fall within the scope of the structures recited in independent claim 1. Claim 2 therefore impermissibly broadens the scope of the claimed invention to read on a process including monomers outside the scope of the CH2=CH-(X) as defined in claim 1.
Applicant may cancel the claim(s), amend the claim(s) to place the claim(s) in proper dependent form, rewrite the claim(s) in independent form, or present a sufficient showing that the dependent claim(s) complies with the statutory requirements.
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.
The factual inquiries for establishing a background for determining obviousness under 35 U.S.C. 103 are summarized as follows:
1. Determining the scope and contents of the prior art.
2. Ascertaining the differences between the prior art and the claims at issue.
3. Resolving the level of ordinary skill in the pertinent art.
4. Considering objective evidence present in the application indicating obviousness or nonobviousness.
Claim(s) 1-5, 8-12, 14, 15, 17, and 18 are rejected under 35 U.S.C. 103 as being unpatentable over Suzuki et al, US2006/0178486, in view of Tasdelen et al, Progress in Polymer Science vol. 36 (2011).
Example 3 of Suzuki (¶0304-0310; 0289-0296) discloses the production of a diblock copolymer (for claim 1) comprising a polypropylene block, corresponding to the claimed nonpolar block (for claim 1), and a polyacrylic acid block, corresponding to the claimed polar block (for claim 1), via a process comprising the steps of
Polymerizing propylene in the presence of triisobutylaluminum, corresponding to the claimed alkyl aluminum chain transfer agent, followed by heating to produce a polypropylene having a terminal double bond (¶0292-0294), corresponding to the claimed polymerizing step (for claim 1);
Reacting the polypropylene having a terminal double bond with a boron-containing compound, followed by a functionalization reaction to prepare a hydroxy-terminated polypropylene (¶0296);
Reacting said hydroxy-terminated polypropylene with 2-bromopriopionyl chloride, corresponding to the claimed linker to form a macroinitiator (¶0305), corresponding to the claimed producing step (for claim 1);
Polymerizing butyl acrylate, corresponding to claimed monomer CH2=CH-(X) (for claims 1, 3) in the presence of said macroinitiator and cuprous bromide (i.e., CuBr) (for claims 11, 12) (¶0307-0308), corresponding to the claimed radical reagent (for claim 1), to form a diblock copolymer, corresponding to the second claimed reacting step (for claim 1); and
Hydrolyzing the polymer at 96 °C to convert the t-butyl groups to acid groups (for claim 4) (¶0308).
Regarding claim 2: As noted above, the prior art process uses the monomer t-butyl acrylate in the polymerization of the second block. This corresponds to the claimed monomer CH2=CHC(O)(O)R wherein R is a C4 branched alkyl.
Regarding claim 9: The polypropylene block of the prior art copolymer may comprise propylene, corresponding to the claimed C3 olefin, and ethylene (¶0032, 0034, 0035).
Regarding claims 10: As noted above, the prior art process uses the compound 2-bromopropionyl chloride, corresponding to the claimed linker wherein the halogen at the alpha carbon is bromine.
Regarding claim 14: As noted above, the prior art process uses triisobutylaluminum, corresponding to claimed formula AlR3 wherein each R is a C4 alkyl.
Regarding claim 15: As noted above, the prior art process comprises the same step of heating a polymer/aluminum species to form a terminal double bond as in the recited process.
Regarding claim 17: The fourth step of the prior art process results in a polypropylene-b-poly(t-butyl acrylate) diblock copolymer.
Regarding claim 18: As noted above, Suzuki teaches the production of a polymer via a process comprising polymerization of propylene to form a first block, followed by polymerization of (meth)acrylate to form a second block. It has been held that compounds which are homologs (compounds differing regularly by the successive addition of the same chemical group, e.g., by -CH2- groups) are generally of sufficiently close structural similarity that there is a presumed expectation that such compounds possess similar properties; see In re Wilder, 563 F.2d 457, 195 USPQ 426 (CCPA 1977) (MPEP § 2144.09(II)). Note that propylene and ethylene are homologs-both are linear alkenes whose structures differ from the presence of a single -CH2- group. Furthermore, the two compounds are polymerizable via the same radical methods through the double bond in their structures. Given the structural similarity of the two compounds and the fact that they are known to be polymerizable via the same methods, one of ordinary skill in the art would reasonably expect that the prior art method could be performed using ethylene as the monomer in the first block. Barring a showing of evidence demonstrating unexpected results, it therefore would have been obvious to modify the process of Suzuki to make an ethylene/acrylate diblock copolymer.
Suzuki is silent regarding the step of reacting the polymer having a terminal double bond with a thiol compound.
As taught by Tasdelen, it was known in the art that mercaptoethanol, corresponding to the claimed thiol compound (for claim 1), could be reacted with a polymer having a terminal double bond via a Click reaction (for claim 8) as a convenient method of preparing a hydroxy monotelechelic polymer (page 536: right column 2nd paragraph).
Regarding claim 5: Mercaptoethanol corresponds to the claimed structure wherein x is 2 and Y is -OH.
Suzuki discloses a process of making a diblock copolymer, wherein said process comprises a step of reacting a polypropylene having a terminal double bond with a boron-containing compound to introduce a terminal hydroxyl group. Said terminal hydroxyl group is then reacted to form a make the polypropylene into a macroinitiator that can be used to initiate polymerization of the monomer(s) for the second block.
As taught by Tasdelen, it was known in the art that polymers having a terminal double bond could be modified via reaction with mercaptoethanol in order to introduce a terminal hydroxyl group. Barring a showing of evidence demonstrating unexpected results, it therefore would have been obvious to one of ordinary skill in the art before the effective filing date to modify the process of Suzuki by substituting mercaptoethanol for the boron-containing compound in the second step of the prior art process, with the reasonable expectation of obtaining a polypropylene having a terminal hydroxyl group that could then be reacted with 2-bromopriopionyl chloride to form a macroinitiator for use in the preparation of the second block.
Claim 16 is rejected under 35 U.S.C. 103 as being unpatentable over the combination of Suzuki et al, US2006/0178486, and Tasdelen et al, Progress in Polymer Science vol. 36 (2011as applied to claims 1-5, 8-12, 14, 15, 17, and 18 above, and further in view of Fan et al, Journal of Polymer Science Part A: Polymer Chemistry vol. 49 (2011).
As discussed earlier in this Action, the combination of Suzuki in view of Tasdelene renders obvious the production of a polypropylene/polyacrylic acid diblock copolymer via a process comprising the steps of
Polymerizing propylene in the presence of triisobutylaluminum, corresponding to the claimed alkyl aluminum chain transfer agent, followed by heating to produce a polypropylene having a terminal double bond, corresponding to the claimed polymerizing step;
Reacting the polypropylene having a terminal double bond with mercaptoethanol to prepare a hydroxy-terminated polypropylene;
Reacting said hydroxy-terminated polypropylene with 2-bromopriopionyl chloride, corresponding to the claimed linker to form a macroinitiator, corresponding to the claimed producing step;
Polymerizing butyl acrylate, corresponding to claimed monomer CH2=CH-(X) in the presence of said macroinitiator and cuprous bromide (i.e., CuBr), corresponding to the claimed radical reagent, to form a diblock copolymer, corresponding to the second claimed reacting step; and
Hydrolyzing the polymer at 96 °C to convert the t-butyl groups to acid groups.
Suzuki is silent regarding the use of a compound corresponding to recited formula (II).
Fan discloses the production of macromolecular brushes comprising block copolymers side chains, wherein said side chains are prepared via a process wherein terminal hydroxyl group(s) are converted to macroinitiator(s) which are then used to initiate the polymerization of unsaturated monomer(s) to form the second block (abstract; Scheme 1:2nd row). As taught by Fan, it was known in the art that 2-bromoisobutyryl bromide, corresponding to the claimed formula (II) X1 and X2 are both bromine and R1 and R2 are both C1 hydrocarbon groups (for claim 16), was suitable for use as a reagent that could be reacted with hydroxyl groups to form such macroinitiators.
Suzuki and Fan both disclose the production of block copolymer structures via processes wherein a first polymer having hydroxyl groups is converted into a macroinitiator via an esterification reaction with an acryl halide. As taught by Fan, it was known in the art that 2-bromoisobutyryl bromide could be used as the acyl halide in such reactions. Barring a showing of evidence demonstrating unexpected results, it therefore would have been obvious to modify the process taught by the combination of Suzuki and Tasdelen by substituting the 2--bromopriopionyl chloride with 2-bromoisobutyryl bromide, with the reasonable expectation of obtaining a modified polymer that could be used as a macroinitiator for the polymerization of monomers for the second block.
Claim(s) 1-18 are rejected under 35 U.S.C. 103 as being unpatentable over Suzuki et al, US2006/0178486, in view of Limer et al, Macromolecules vol. 39 (2006) and Lowe, Polymer Chemistry vol. 5 (2014).
The disclosure of Suzuki is discussed in paragraphs 17-24 of this Action, incorporated here by reference (for claims 1-5, 8-12, 14, 15, 17, 18).
Briefly, Suzuki discloses the production of a polypropylene/polyacrylic acid diblock copolymer (for claim 1) comprising a polypropylene block, corresponding to the claimed nonpolar block (for claim 1), and a polyacrylic acid block, corresponding to the claimed polar block (for claim 1), via a process comprising the steps of
Polymerizing propylene in the presence of triisobutylaluminum, corresponding to the claimed alkyl aluminum chain transfer agent, followed by heating to produce a polypropylene having a terminal double bond, corresponding to the claimed polymerizing step (for claim 1);
Reacting the polypropylene having a terminal double bond with a boron-containing compound, followed by a functionalization reaction to prepare a hydroxy-terminated polypropylene;
Reacting said hydroxy-terminated polypropylene with 2-bromopriopionyl chloride, corresponding to the claimed linker to form a macroinitiator, corresponding to the claimed producing step (for claim 1);
Polymerizing butyl acrylate, corresponding to claimed monomer CH2=CH-(X) (for claim 1) in the presence of said macroinitiator and cuprous bromide (i.e., CuBr), corresponding to the claimed radical reagent (for claim 1), to form a diblock copolymer, corresponding to the second claimed reacting step (for claim 1); and
Hydrolyzing the polymer at 96 °C to convert the t-butyl groups to acid groups.
Suzuki is silent regarding the step of reacting the polymer having a terminal double bond with a thiol compound.
Limer teaches that it was known in the art that polymers having a terminal amine group could be reacted with acyl halides such as 2-bromoisobutyryl bromide, corresponding to claimed formula (II) as discussed in paragraph 33 of this Action (for claim 16), in order to form a macroinitiator that could then be used to initiate the polymerization of monomers for the production of a block copolymer (page 1354: right column, 3rd paragraph; page 1357: left column, 3rd paragraph).
Lowe teaches that it was known in the art that thiol compounds having a protected amine such as Boc-protected cysteamine, corresponding to the thiol compound (for claim 1) of the claimed formula wherein x is 2, Y is -NHRB, and RB is the Boc protecting group (for claims 5-6), could be reacted with double bonds present in polymers via a Click reaction, followed by removal of the Boc group (i.e., deprotection) (for claim 7) to introduce amine groups into a polymer structure (page 4830: left column, lines 31-39 and Fig. 8).
Suzuki discloses a process of making a diblock copolymer, wherein said process comprises a step of converting the terminal double bond of a polypropylene to a macroinitiator via reaction with an acryl halide. As taught by Limer, it was known in the art that such acyl halides such as 2-bromoisobutyryl bromide could also be reacted with polymers having terminal amine groups in order to form such macroinitiators. As taught by Lowe, it also known in the art that polymers having unsaturated bonds could be reacted protected amine-containing thiol compounds such as Boc-cysteamine via Click chemistry in order to introduce amine groups.
Barring a showing of evidence demonstrating unexpected results, it therefore would have been obvious to one of ordinary skill in the art to modify the process of Suzuki by substituting Boc-cysteamine for the boron-containing compound and 2-bromoisobutyryl bromide for the 2-bromopriopionyl chloride, with the reasonable expectation of obtaining a polypropylene wherein the terminal double bond had been converted to a macroinitiator structure that could be used to polymerize the monomer(s) for the second block of the diblock copolymer.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to JEFFREY S LENIHAN whose telephone number is (571)270-5452. The examiner can normally be reached Mon.-Fri. 5:30-2:00PM.
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/JEFFREY S LENIHAN/Primary Examiner, Art Unit 1765
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