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 .
Election/Restrictions
Applicant's election with traverse of Group I (claims 17-29) in the reply filed on March 10, 2026 is acknowledged. The traversal is on the ground(s) that the special technical feature is reflected in claim 17, the process of which was shown in the as-filed specification to improve the optical properties of transparent copolyamides from lactams. This argument is not found persuasive because the copolyamide is a shared technical feature of the claims. Group I is a method of making a copolyamide, Group II (claim 30) is the copolyamide obtained from the method of Group I, and Group III (claims 31-32) is a method of using the copolyamide of Group II. Applicant has not demonstrated that the prior art copolyamide is patentably distinct from a copolyamide produced by the process of claim 17. It is noted that while claim 30 claims a copolyamide obtainable by the process according to claim 17, case law holds that:
Even though product-by-process claims are limited by and defined by the process, determination of patentability is based on the product itself. The patentability of a product does not depend on its method of production. If the product in the product-by-process claim is the same as or obvious from a product of the prior art, the claim is unpatentable even though the prior product was made by a different process. See In re Thorpe, 777 F.2d 695, 698, 227 USPQ 964, 966 (Fed. Cir. 1985).
To the extent that the process limitations in a product-by-process claim do not carry weight absent a showing of criticality, the reference discloses the claimed product in the sense that the prior art product structure is seen to be no different from that indicated by the claims. The prior art teaches the same product as the instant claims, regardless of the process by which the prior art product has been produced. The burden is shifted to Applicant to provide factually supported evidence which demonstrates the contrary.
The requirement is still deemed proper and is therefore made FINAL.
Claims 30-32 are withdrawn from further consideration pursuant to 37 CFR 1.142(b), as being drawn to a nonelected inventions, there being no allowable generic or linking claim.
Claim Objections
Claim 29 is objected to because of the following informalities:
Claim 29 comprises the limitation “(ac) the liquid phase from the helical tube of step (aa), mixed with the organic components of step (ab)” in the last two lines. This limitation is grammatically incorrect. Based on specification page 16, lines 9-17, it is suggested that Applicant may have intended the limitation to read “(ac) the liquid phase from the helical tube of step (aa) is mixed with the organic components of step (ab).”
Appropriate correction is required.
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.
Claims 17, 19-20, 22, and 24-29 are rejected under 35 U.S.C. 103 as being unpatentable over Nielinger (US 5,013,518, cite no. 2 on 5/26/2023 IDS) in view of Plachetta (US 2011/0245435 A1, cite no. 1 on 5/26/2023 IDS).
Regarding claims 17, 22, and 24-29, Nielinger teaches a process of continuously preparing copolyamides (Nielinger, col. 2, lines 5-8). The copolyamides are prepared by polymerizing ε-caprolactam, dimerized fatty acid and a diamine (Nielinger, col. 1, lines 46-49). Nielinger’s ε-caprolactam reads on the instant lactam (A) is 6-aminohexanolactam (claims 24-25). The dimerized fatty acids are prepared by condensation of unsaturated fatty acids containing 16-20 carbon atoms (Nielinger, col. 1, lines 55-61) and read on the instant at least one C32-C40 dimer acid (B1). The preferred amines include hexamethylene diamine (Nielinger, col. 2, lines 3-4). Hexamethylene reads on a C6 diamine (B2) that is 1,6-diaminohexane (claims 26-27). The dimer acid and diamine are used in approximately equivalent quantities (Nielinger, col. 1, lines 52-53) (claim 22). Because none of the monomers listed by Nielinger comprise polyoxyalkene groups, it would have been obvious to one of ordinary skill in the art to use monomers not comprising polyoxyalkylene groups (claim 28).
Nielinger further teaches that the copolyamide may be prepared continuously in a VK tube (Nielinger, col. 2, lines 8-9), but provides no detail on how to prepare the copolyamide using a VK tube.
In comparison to claim 1, Nielinger does not teach step a) mixing the lactam with the monomers at a temperature of 60-150 °C and does not specify that the VK tube is used vertically with the mixture passed from the top downward.
However, Plachetta teaches a continuous process for preparing copolyamides from lactams and salts of diamines and dicarboxylic acids in which the random distribution of the monomer units is improved (Plachetta, [0004]). In particular, Plachetta teaches that the comonomer units are distributed more randomly in the polymer chain than is possible by other known processes (Plachetta, [0010]). Copolyamides produced by this method also have the advantage of having improved product properties, such as lower intrinsic color (Plachetta, [0010]). Plachetta’s method utilizes vertical polymerization tubes that are referred to as VK tubes (Plachetta, [0030]). Plachetta’s method comprises the following steps (Plachetta, [0006-0009]):
a) mixing an aqueous solution of lactams with salts of diamines and dicarboxylic acids under elevated pressure at a temperature of from 80 to 300° C,
b) feeding the mixture thus obtained to a heated helical tube evaporator in which a liquid phase and a vapor phase form at a temperature of from 140 to 300° C., a stream of water vapor and/or inert gas also being introduced into the mixture if appropriate upstream of the helical tube,
c) removing the vapor phase formed in stage b) from the liquid phase and separating it in a column into water vapor and into organic components comprising diamines, dicarboxylic acids and lactams, and recycling the organic components
into the polymerization, and
d) passing the liquid phase from the helical tube of stage b) mixed with the organic components of stage c) from the top downward through a vertical polymerization tube at polyamide-forming temperatures to obtain a copolyamide.
Plachetta’s step a is similar to instant step a), but differs in that it teaches a broader temperature range. Plachetta’s step b reads on instant step (aa). Rep’s step c reads on instant step (ab) and step (ac). Plachetta’s step d reads on instant step b).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have copolymerized the lactam and monomer components of Nielinger using the method of Plachetta in order to achieve a random monomer distribution and execute Nielinger’s teaching of preparing the copolyamide in a VK tube. One would have had a reasonable expectation of success because, like Nielinger, Plachetta teaches polymerizing lactams with equimolar amounts of diacids and diamines (Nielinger, [0016]) to form copolyamides using a VK tube. The resulting method satisfies step b) as well as steps (aa), (ab), and (ac) of claim 29.
Modified Nielinger does not anticipate a temperature of 60-150 °C in step a).
However, modified Nielinger teaches a temperature of 80 to 300° C. It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have selected any temperature in the range of 80 to 300° C because Nielinger in view of Plachetta teaches this temperature range. It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
Regarding claim 19, modified Nielinger teaches the process of claim 17 where the dimerized fatty acids are prepared by condensation of unsaturated fatty acids containing 16-20 carbon atoms (Nielinger, col. 1, lines 55-61). Given that Nielinger teaches that the dimer acid is produced from unsaturated C16-C20 fatty acids, if would have been obvious to one ordinary skill to select a dimer acid mixture obtainable by dimerizing unsaturated C16, C18, and/or C20 fatty acids.
Regarding claim 20, modified Nielinger teaches the process of claim 17 where step a) comprises mixing an aqueous solution of ε-caprolactam and salts of C32-C40 dimer acids and 1,6-diaminohexane, as discussed above.
Modified Nielinger differs from instant claim 20 in that the order of mixing is not explicitly stated.
However, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have formed a mixture of ε-caprolactam and salts of C32-C40 dimer acids and 1,6-diaminohexane as taught by modified Nielinger, by mixing Nielinger’s disclosed components together utilizing any order of addition, including initially charging the lactam and adding the monomers together. One would have had a reasonable expectation of success in utilizing any order of mixing because the same desired combination of the components is ultimately obtained, and there is nothing of record to suggest that the order of mixing is critical to the process of preparing a mixture of the lactam and monomers. Case law has established that selection of any order of performing process steps is prima facia obvious in the absence of new or unexpected results (see MPEP § 2144.04, IV. C.).
Claims 17-29 are rejected under 35 U.S.C. 103 as being unpatentable over Minkwitz (US 2019/0269075 A1, cite no. 2 on 5/26/2023 IDS) in view of Plachetta (US 2011/0245435 A1, cite no. 1 on 5/26/2023 IDS).
Regarding claims 17, 19, 24-27, and 29, Minkwitz teaches a process for preparing copolyamides by copolymerizing (A) 5-99 wt% of at least one lactam and (B) 1-95 wt% of a monomer mixture (M) comprising (B1) at least one C32-C40 dimer acid and (B2) at least one C4-C12 diamine (Minkwitz, [0068-0072]).
In the working examples, Minkwitz exemplifies polymerizing a combination of caprolactam, C36 dimer acid, and hexamethylenediamine (Minkwitz, [0309-0318]). Caprolactam reads on the instant lactam (A) is 6-aminohexanolactam (Minkwitz, [0114]) (claims 24-25). Minkwitz teaches that the C36 dimer acid is preferably prepared from unsaturated C18 fatty acids (Minkwitz, [0147]), reading on claim 19. Hexamethylene reads on a C6 diamine (B2) that is 1,6-diaminohexane (claims 26-27).
In the examples (Minkwitz, [0309-0318]), Minkwitz combines caprolactam, C36 dimer, an 85 wt% hexamethylenediamine in water solution, and water and stirs the mixture at 290 °C for 11 hours to produce the copolyamide.
Minkwitz’s method differs from the claimed method in that Minkwitz does not teach the steps of a) mixing the lactam with monomers at a temperature of 60 to 150 °C and b) passing the mixture obtained in step a) from the top downward through a vertical polymerization tube at polyamide-forming temperatures to obtain a copolyamide.
However, Minkwitz teaches that the polymerization can take place in any reactors known to those skilled in the art (Minkwitz, [0096]). Therefore, it would have been obvious to one of ordinary skill that the polymerization could be performed in other types of reactors according to other methods. In addition, Minkwitz teaches that the copolyamide is preferably a random copolymer (Minkwitz, [0084]), so one of ordinary skill would have understood that methods of random polymerization are desirable.
Plachetta teaches a continuous process for preparing copolyamides from lactams and salts of diamines and dicarboxylic acids in which the random distribution of the monomer units is improved (Plachetta, [0004]). In particular, Plachetta teaches that the comonomer units are distributed more randomly in the polymer chain than is possible by other known processes (Plachetta, [0010]). Copolyamides produced by this method also have the advantage of having improved product properties, such as lower intrinsic color (Plachetta, [0010]). Plachetta’s method utilizes vertical polymerization tubes that are referred to as VK tubes (Plachetta, [0030]) and comprises the following steps (Plachetta, [0006-0009]):
a) mixing an aqueous solution of lactams with salts of diamines and dicarboxylic acids under elevated pressure at a temperature of from 80 to 300° C,
b) feeding the mixture thus obtained to a heated helical tube evaporator in which a liquid phase and a vapor phase form at a temperature of from 140 to 300° C., a stream of water vapor and/or inert gas also being introduced into the mixture if appropriate upstream of the helical tube,
c) removing the vapor phase formed in stage b) from the liquid phase and separating it in a column into water vapor and into organic components comprising diamines, dicarboxylic acids and lactams, and recycling the organic components
into the polymerization, and
d) passing the liquid phase from the helical tube of stage b) mixed with the organic components of stage c) from the top downward through a vertical polymerization tube at polyamide-forming temperatures to obtain a copolyamide.
Plachetta’s step a is similar to instant step a), but differs in that it teaches a broader temperature range. Plachetta’s step b reads on instant step (aa). Rep’s step c reads on instant step (ab) and step (ac). Plachetta’s step d reads on instant step b).
It would have been obvious to one of ordinary skill in the art prior to the effective filing date of the claimed invention to have copolymerized the lactam and monomer components of Minkwitz using the method of Plachetta, including the steps of mixing at a temperature of 80-300 °C, concentrating the solution as described in Plachetta’s steps b and c, and polymerizing the solution as described in Plachetta’s step d. One would have been motivated to use Plachetta’s method in order to achieve a random monomer distribution and achieve lower intrinsic color. One would have had a reasonable expectation of successfully producing a copolyamide useful in films because, like Minkwitz, Plachetta teaches polymerizing lactams, diacids, and diamines to form copolyamides that are used in films (Minkwitz, abstract; Plachetta, [0037]). The resulting method is continuous and satisfies step b) and steps (aa), (ab), and (ac) of claim 29.
Modified Minkwitz does not anticipate a temperature of 60-150 °C in step a).
However, modified Minkwitz teaches a temperature of 80 to 300° C. It would have been obvious to one of ordinary skill in the art prior to the effective filing date to have selected any temperature in the range of 80 to 300° C because Minkwitz in view of Plachetta teaches this temperature range. It would have been obvious to one of ordinary skill in the art before the effective filing date of the invention to have selected the overlapping portion of the ranges disclosed by the reference because selection of overlapping portion of ranges has been held to be a prima facie case of obviousness. See MPEP § 2144.05.I.
Regarding claims 18 and 20, modified Minkwitz teaches the process of claim 17 where step a) comprises mixing an aqueous solution of caprolactam, C36 dimer acid, and hexamethylenediamine (Minkwitz, [0316]).
Modified Minkwitz does not specify the order of mixing.
However, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have formed a mixture of caprolactam, C36 dimer acid, hexamethylenediamine, and water as taught by Minkwitz, by mixing Minkwitz’s disclosed components together utilizing any order of addition. Orders of addition include initially charging the lactam (caprolactam) and adding the monomers (C36 dimer acid and hexamethylenediamine) separately or together, as recited in claim 20, or premixing of the at least one lactam (caprolactam) with component (B1) (C36 dimer acid) to obtain a premixture and subsequently adding component (B2) (hexamethylenediamine), as recited in claim 18. One would have had a reasonable expectation of success in utilizing any order of mixing because the same desired combination of the components is ultimately obtained, and there is nothing of record to suggest that the order of mixing is critical to the process of preparing a mixture of the lactam and monomers. Case law has established that selection of any order of performing process steps is prima facia obvious in the absence of new or unexpected results (see MPEP § 2144.04, IV. C.).
Regarding claims 21-23, modified Minkwitz teaches the process of claim 17. In example C-3, Minkwitz exemplifies copolyamides derived from a combination of 932 kg of caprolactam, 323.2 kg of C36 dimer acid, and 66.2 of kg hexamethylenediamine (Minkwitz, [0316] where 85% of 77.84 kg is about 66.2 kg). The caprolactam is present in an amount of about 70.5 wt% (932/(932+323.2+66.2)=0.705) and the monomers are present in an amount of about 29.5 wt% (claim 23). The molar number of the amine groups from (B2) is essentially equal to the molar number of the sum total of the carboxyl groups from (B1) (323.2 kg/0.57kg/mole = 567 moles diacid and 66.2kg/0.116kg/mol = 570 moles diamine) (claim 22).
Hexamethylene diamine is provided in an 85 wt% aqueous solution (Minkwitz, [0316]). Because Minkwitz is silent as to any water content in the C36 dimer acid, it would be obvious to one of ordinary skill to use a C36 with a negligible amount of water. The total amount of water in the monomer is therefore about 3 wt% (77.84*0.15/(77.84+323.2)=0.029), satisfying the requirement of 0-5 wt% water in the monomer (claim 21). Because Minkwitz is silent as to any water content in the caprolactam, it would be obvious to one of ordinary skill to use a caprolactam with a negligible amount of water, satisfying the requirement of 0-10 wt% water (claim 21).
Regarding claim 28, modified Minkwitz teaches the process of claim 17 where the copolyamide is prepared from a lactam, a dimer acid, and a diamine. Minkwitz exemplifies a combination of caprolactam, C36 dimer acid, and hexamethylenediamine without any polyoxyalkylene monomers in the working examples and makes no mention of utilizing polyoxyalkylene monomers in the broader disclosure. Therefore, it would have been obvious to one of ordinary skill in the art prior to the effective filing date to have prepared the copolyamide by a method wherein the monomers do not comprise polyoxyalkylene groups.
Relevant Art Cited
Additional prior art documents which are relevant to Applicants’ invention can be found on the attached PTO-892 form. US-2020/0123335-A1 and US-20190224902-A1 teach copolyamides with the same content of lactam, C4-C20 diamine, and C32-C40 dimer acid as instant claim 23.
Conclusion
Any inquiry concerning this communication or earlier communications from the examiner should be directed to AUDRA DESTEFANO whose telephone number is (703)756-1404. The examiner can normally be reached Monday-Friday 9-5.
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/AUDRA J DESTEFANO/Examiner, Art Unit 1766
/RANDY P GULAKOWSKI/Supervisory Patent Examiner, Art Unit 1766
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