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 1-16 are pending as amended on 6/13/2023.
Election/Restrictions
Applicant’s election without traverse of telechelic polyamide species:
containing at least some tertiary amide linkages,
containing no heteroatom linkages other than amide linkages,
containing repeating units derived from lactam/aminocarboxylic acid monomer, and
wherein at least 70 mol% of the polyamide has exactly two carboxylic acid end groups,
in the reply filed on 4/13/2026 is acknowledged.
Claims 9, 10, 15 and 16 are withdrawn from further consideration pursuant to 37 CFR 1.142(b) as being drawn to a nonelected species, there being no allowable generic or linking claim.
Claim Objections
Claim 1 is objected to because of the following informalities:
Claim 1 contains repetitive language which makes the claim challenging to read.
Claim 1 is copied below. Language which the Examiner believes to be redundant is shown struck-through. Applicant is not required to amend the claim by deleting language exactly according to the example below, however, Applicant is requested to review claim 1 and remove redundant language.
PNG
media_image1.png
424
707
media_image1.png
Greyscale
Additionally, claim 1 recites “repeat units derived from polymerizing dicarboxylic acid monomeric units with monomeric units of at least one other monomer type…” This language is objected to because a “monomer” is polymerized, while a “monomeric unit” (like a repeat unit) is the structure within a polymer that results from the polymerization of a monomer. Applicant is requested to amend claim 1 (as well as similarly problematic dependent claims 4-7) to utilize terms such as “monomer” and “monomeric unit” according to their conventional meanings.
Appropriate correction is required.
Claim Rejections - 35 USC § 112
The following is a quotation of 35 U.S.C. 112(b):
(b) CONCLUSION.—The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the inventor or a joint inventor regards as the invention.
The following is a quotation of 35 U.S.C. 112 (pre-AIA ), second paragraph:
The specification shall conclude with one or more claims particularly pointing out and distinctly claiming the subject matter which the applicant regards as his invention.
Claims 1, 3-8 and 11-14 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 1 recites (last two lines) “…wherein at least 20 mole percent of the telechelic polyamide has exactly two functional end groups of the same functional type comprising amino end groups or carboxylic end groups.” The use of the open-ended term “comprising” renders the scope of the claim unclear, because it is not clear whether the recited alternatives for the “two functional end groups” could include a type of group other than the recited “amino end groups or carboxylic end groups.” Claims 3-8 and 11-14 are unclear for the same reason because they fail to remedy the issue in claim 1. Note that claim 2 recites that the functional end groups are “selected from the group consisting of amino or carboxylic end groups.” Claim 2 is clear with respect to the recited end groups, because it recites a closed group of alternatives. See MPEP 2173.05(h) for further guidance.
Claims 4 and 5 further limit the polyamide by requiring that the amide linkages “comprise at least 50 wt% of the telechelic polyamide” (claim 4) or “comprise at least 80 wt% of the telechelic polyamide.” It is not clear how at least 50 wt%, or at least 80 wt%, of the total weight of the polyamide could be made up of just the “amide linkages” (i.e., -C(O)NH- groups) in the polyamide. Perhaps Applicant intended to recite a weight percentage of amide linkages based on the total weight of all linkages connecting monomeric units within the polyamide (rather than based on the weight of the entire polyamide). Alternatively, Applicant may have intended to recite a weight percentage of repeat units connected by amide linkages (rather than a weight percentage of amide linkages), based on the weight of the entire polyamide. Because the claim as worded does not make logical sense, and because it is not possible to determine the intended scope of the claim, the claims are deemed indefinite. For examination purposes, claim 4 has been interpreted as reciting a polyamide wherein at least 50 wt% of linkages between monomeric units are amide linkages.
Claim Rejections - 35 USC § 102
The following is a quotation of the appropriate paragraphs of 35 U.S.C. 102 that form the basis for the rejections under this section made in this Office action:
A person shall be entitled to a patent unless –
(a)(1) the claimed invention was patented, described in a printed publication, or in public use, on sale, or otherwise available to the public before the effective filing date of the claimed invention.
Claim(s) 1, 2 and 4-8 is/are rejected under 35 U.S.C. 102(a)(1) as being anticipated by Coquard et al (US 4343743).
NOTE: this rejection establishes that Coquard anticipates embodiments encompassed by generic claims. This is not a rejection of the elected species, because Coquard does not disclose tertiary amide linkages.)
As to claims 1, 2, 4, 5 and 8, Coquard discloses a prepolyamide having a molecular weight of 3000 and containing COOH end groups, formed from reaction of a molar excess of dimeric acid with hexamethylenediamine (col 6, example 2, lines 10-20). The dimeric acid is Empol 1010 (col 5, lines 54-59), which is a C36 dimer acid, and has a monofunctional content of 0.03% and trimer content of 3%.
The prepolyamide exemplified by Coquard has repeat units derived from polymerizing dicarboxylic acid monomer, wherein substantially all of the dicarboxylic acid monomer is dimeric fatty acid monomer, and wherein the other monomer is a diamine monomer (hexamethylenediamine). Therefore, all (100%) of the linkages in Coquard’s prepolyamide are amide linkages (within the presently claimed range of at least 10% recited in claim 1, at least 50 wt% as recited in claim 4, and at least 80 wt% in claim 5). Given that the diamine monomer has primary amine groups and no reagent is utilized which would result in a tertiary amine group, there is reasonable basis to conclude that none of the amide linkages are tertiary amide linkages (within the presently claimed range of less than 25%). Given that the diamine monomer is difunctional and the dimer acid monomer is 97% difunctional, that the dimeric acid is utilized in molar excess, and that Coquard teaches that the prepolyamide has COOH end groups, there is reasonable basis to conclude that substantially all of the prepolyamide has exactly two functional end groups, and that both end groups are carboxylic (within the presently claimed range of at least 20 mole percent recited in claim 1, and at least 70 mole percent in claim 2). In a prepolyamide formed from Empol 1010 and hexamethylenediamine, as exemplified by Coquard, substantially all (within the recited range of at least 50 wt%) of the repeating units have a structure as recited in instant claim 8 wherein Ra is branched C36 alkylene, Rb is linear C6 alkylene, and Rc and Rd are hydrogen.
As to claims 6 and 7, as set forth above, Coquard suggests a prepolyamide having a molecular weight of 3000 and COOH end groups, formed from a C36 dimer acid (molar excess) and hexamethylenediamine. When calculated using a C36 dimer molecular weight of ~570 g/mol, a prepolyamide having a molecular weight of ~3000 g/mol and having a dimer acid-derived unit at each terminal has ~3.5 residues of hexamethylenediamine (MW 116 g/mol) and ~4.5 residues of dimer acid (3.5*116=406; 4.5*570=2565; 2565+406=2971). The content of dimer acid units in the polyamide is ~86 wt% (2565/2971), which falls within the ranges recited in claims 6 and 7.
Claim Rejections - 35 USC § 103
The following is a quotation of 35 U.S.C. 103 which forms the basis for all obviousness rejections set forth in this Office action:
A patent for a claimed invention may not be obtained, notwithstanding that the claimed invention is not identically disclosed as set forth in section 102, if the differences between the claimed invention and the prior art are such that the claimed invention as a whole would have been obvious before the effective filing date of the claimed invention to a person having ordinary skill in the art to which the claimed invention pertains. Patentability shall not be negated by the manner in which the invention was made.
Claim(s) 1-8 and 11-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Coquard et al (US 4343743).
NOTE: this rejection establishes that Coquard suggests embodiments encompassed by generic claims. This is not a rejection of the elected species, because Coquard does not disclose tertiary amide linkages.)
As to claims 1, 2, 4, 5 and 8, Coquard discloses a prepolyamide having a molecular weight of 3000 and containing COOH end groups, formed from reaction of a molar excess of dimeric acid with hexamethylenediamine (col 6, example 2, lines 10-20).
The prepolyamide exemplified by Coquard has repeat units derived from polymerizing dicarboxylic acid monomer (dimeric acid), wherein 100 percent of the dicarboxylic acid monomer is dimeric fatty acid monomer, and wherein the other monomer is a diamine monomer (hexamethylenediamine). No monomers other than a dimeric acid (having two COOH groups) and a diamine (having two amine groups) are utilized to form the prepolymer, and therefore, all (100%) of the linkages in Coquard’s prepolyamide are amide linkages (within the presently claimed range of at least 10% recited in claim 1, at least 50 wt% as recited in claim 4, and at least 80 wt% in claim 5). Given that the diamine monomer has primary amine groups and no reagent is utilized which would result in a tertiary amine group, there is reasonable basis to conclude that none of the amide linkages are tertiary amide linkages (within the presently claimed range of less than 25%). Given that both of the monomers used are difunctional (see also col 1, lines 55-66), that the dimeric acid is utilized in molar excess, and that Coquard teaches that the prepolyamide has COOH end groups, there is reasonable basis to conclude that substantially all of the prepolyamide has exactly two functional end groups, and that both end groups are carboxylic (within the presently claimed range of at least 20 mole percent recited in claim 1, and at least 70 mole percent in claim 2).
As to the recitation that the dicarboxylic acid monomeric units each contain 34-36 carbon atoms:
Coquard teaches that the dimer acids are preferred among diacids having 20-60 carbon atoms (col 2, lines 7-8), which encompasses the presently claimed range of 34-36 carbon atoms. Additionally, Coquard teaches that most advantageous starting materials are derived from oleic and linoleic acids, and having a fraction of dimeric acid greater than 95%, with proportions of monofunctional and higher functional acids being less than 1 wt% and 3 wt%, respectively, preferred (col 2, lines 34-46). Both oleic and linoleic acids have 18 carbon atoms, and therefore, the dimeric acids thereof have 36 carbon atoms (meeting the presently claimed dicarboxylic acid monomer having 34-36 carbon atoms). When selecting reactants to form a prepolyamide, as taught by Coquard, the person having ordinary skill in the art would have been motivated to utilize the starting material taught by Coquard as being “most advantageous” in the broader disclosure in order to ensure the properties and benefits desired by Coquard are ultimately achieved. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a prepolymer from dimeric acid and hexamethylenediamine, as exemplified by Coquard, by utilizing dimeric acid derived from oleic and linoleic acid (i.e., C36 dimer acid) having no monofunctional or trifunctional proportions as the dimer acid monomer, thereby arriving at the presently claimed subject matter. In a prepolyamide formed from dimeric oleic/linoleic acid and hexamethylenediamine, as suggested by Coquard, all (100 wt%) of the repeating units have a structure as recited in instant claim 8 wherein Ra is branched C36 alkylene, Rb is linear C6 alkylene, and Rc and Rd are hydrogen.
As to claim 3, Coquard suggests a difunctional prepolyamide according to claim 1, as set forth above. Coquard further teaches that a proportion of reactants can be replaced with aminoacids or lactams in order to obtain selected mechanical properties (col 3, lines 27-42). It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a prepolyamide from dimer acid and diamine, as suggested by Coquard, by further including lactam or aminocarboxylic in any appropriate amount, as taught by Coquard, in order to impart properties associated therewith, as desired.
As to claims 6 and 7, as set forth above, Coquard suggests a prepolyamide having a molecular weight of 3000 and COOH end groups, formed from a C36 dimer acid (molar excess) and hexamethylenediamine. When calculated using a C36 dimer molecular weight of ~570 g/mol, a prepolyamide having a molecular weight of ~3000 g/mol and having a dimer acid-derived unit at each terminal has ~3.5 residues of hexamethylenediamine (MW 116 g/mol) and ~4.5 residues of dimer acid (3.5*116=406; 4.5*570=2565; 2565+406=2971). The content of dimer acid units in the polyamide is ~86 wt% (2565/2971), which falls within the ranges recited in claims 6 and 7.
As to claims 11 and 12, Coquard discloses that the molecular weight of the polyamide blocks is to be between 500 and 5000 (col 4, lines 16-19). The numerical range disclosed by Coquard falls within the presently claimed ranges, however, Coquard does not specify whether the disclosed molecular weight range is a number average or a weight average. One having ordinary skill in the art would have recognized that the properties of a polymer block depend on the molecular weight thereof. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a polyamide block (prepolyamide), as suggested by Coquard, having both a weight average and number average molecular weight within the range disclosed by Coquard in order to ensure that the polyamide block imparts the properties desired by Coquard to the ultimately obtained block copolymer.
As to claims 13 and 14, Coquard suggests a prepolyamide having a weight average molecular weight of 500 to 5000, as set forth above. Coquard is silent as to the viscosity without solvents in cps at 70 C or 60 C, as recited in claims 13 and 14. However, given that viscosity is an indication of molecular weight, and considering that Coquard suggests a prepolyamide having a structure as described in the instant claims and specification and a molecular weight within the range described in the instant claims and specification, there is reasonable basis to conclude that Coquard suggests a prepolyamide having a molecular weight which corresponds to a viscosity within the presently claimed ranges.
Claim(s) 1-8 and 11-14 is/are rejected under 35 U.S.C. 103 as being unpatentable over Coquard et al (US 4343743) in view of Manuel et al (Segmented block copolymers based on poly(butylene terephthalate) and telechelic polyesters and polyamides of dimerized fatty acids, Polymer, Volume 34, Issue 20, October 1993, Pages 4325-4329).
This is a rejection of the elected species.
The rejection of claims 1-8 and 11-14 over Coquard under 35 USC 103 is incorporated here by reference.
Coquard fails to teach that at least some of the amide linkages in the prepolyamide are tertiary amide linkages.
Like Coquard, Manuel teaches block copolymers which are formed from telechelic polyamides, and based on dimerized fatty acids (p 4325, abstract, title). Manuel teaches that a segment with a low Tg imparts elastomeric properties to the material (p 4325, left). Manuel teaches that Tg is a function of the structure of the repeating monomer units, and that the Tg values of secondary polyamides are lower than Tg values of primary polyamides. The Tg of primary polyamide is high because hydrogen bonds can be formed in the material (p 4327, right column). In Table 1 (p 4327), Manuel shows that a polyamide having primary amine groups, formed from dimer acid and hexamethylenediamine (PPAH1, PPAH2), has a higher Tg than an analogous polyamide having tertiary amide groups, formed from dimer acid and N,N’-dimethylhexamethylenediamine (SPAH1).
Considering Coquard’s disclosure that, for certain applications, there is a need for thermoplastic elastomers which remain pliable down to temperatures below -30 C (col 1, lines 30-34), the person having ordinary skill in the art would have been motivated to modify Coquard’s prepolyamide by substituting any appropriate amount of the amide groups for tertiary amide groups (e.g., by substituting any appropriate proportion of the hexamethylenediamine monomer for N,N’-dimethylhexamethylenediamine monomer) in order to achieve any desired degree of reduction in hydrogen bond formation, and correspondingly any desired reduction in Tg and improvement in pliability at low temperature. It would have been obvious to the person having ordinary skill in the art, therefore, to have formed a prepolyamide from dimer acid and hexamethylenediamine, as suggested by Coquard, by substituting any appropriate amount of Coquard’s hexamethylenediamine for Manuel’s N,N’-dimethylhexamethylenediamine, including an amount corresponding to a presence of tertiary amide linkages within the presently claimed range of less than 25% of amide linkages.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to RACHEL KAHN whose telephone number is (571)270-7346. The examiner can normally be reached Monday to Friday, 8-5.
Examiner interviews are available via telephone, in-person, and video conferencing using a USPTO supplied web-based collaboration tool. To schedule an interview, applicant is encouraged to use the USPTO Automated Interview Request (AIR) at http://www.uspto.gov/interviewpractice.
If attempts to reach the examiner by telephone are unsuccessful, the examiner’s supervisor, Randy Gulakowski can be reached at 571-272-1302. The fax phone number for the organization where this application or proceeding is assigned is 571-273-8300.
Information regarding the status of published or unpublished applications may be obtained from Patent Center. Unpublished application information in Patent Center is available to registered users. To file and manage patent submissions in Patent Center, visit: https://patentcenter.uspto.gov. Visit https://www.uspto.gov/patents/apply/patent-center for more information about Patent Center and https://www.uspto.gov/patents/docx for information about filing in DOCX format. For additional questions, contact the Electronic Business Center (EBC) at 866-217-9197 (toll-free). If you would like assistance from a USPTO Customer Service Representative, call 800-786-9199 (IN USA OR CANADA) or 571-272-1000.
/RACHEL KAHN/ Primary Examiner, Art Unit 1766
Prosecution Insights