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 .
The Office Action is in response to the application filed November 09, 2023.
Claim Analysis
Summary of Claim 1:
A process for the preparation of a functionalized terpolymer having a general formula (I):
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in which:
- R1 and R2, the same or different from each other, represent a hydrogen atom; or they are selected from C1-C30 alkyl groups, preferably C1-C20, linear or branched, saturated, optionally containing heteroatoms, optionally substituted aryl groups, optionally substituted heteroaryl groups, optionally substituted cycloalkyl groups, optionally substituted heterocyclic groups;
- or R1 and R2, can optionally be bonded together so as to form, together with the other atoms to which they are bonded, a cycle containing from 1 to 12 carbon atoms, saturated, optionally substituted with linear or branched C1-C20 alkyl groups, saturated, optionally containing heteroatoms, optionally substituted aryl groups, optionally substituted heteroaryl groups, optionally substituted cycloalkyl groups, optionally substituted heterocyclic groups, trialkyl- or triaryl-silyl groups, dialkyl- or diaryl- amino groups, dialkyl- or diaryl-phosphine groups C1-C20 alkoxy groups, preferably C1-C10, linear or branched, saturated, optionally substituted aryloxy groups, optionally substituted thioalkoxyl or thioaryloxy groups, cyano groups, said cycle optionally containing heteroatoms such as, for example, oxygen, sulphur, nitrogen, silicon, phosphorus, selenium, preferably oxygen, nitrogen;
- R3 and R4, the same or different from each other, represent a hydrogen atom; or they are selected from C1-C30, alkyl groups, preferably C1-C20, linear or branched, saturated or unsaturated, optionally containing heteroatoms, optionally substituted aryl groups, optionally substituted heteroaryl groups, optionally substituted cycloalkyl groups, optionally substituted heterocyclic groups; provided that at least one of R3 and R4 is different from hydrogen and that at least one of R3 and R4 contains at least a double or a triple bond between two adjacent carbon atoms, and in the event that two or more double or triple bonds are present; said bonds can be conjugated or unconjugated, preferably unconjugated;
- or R3 and R4, can optionally be bonded together so as to form, together with the other atoms to which they are bonded, a cycle containing from 1 to 12 carbon atoms, saturated or unsaturated, optionally substituted with C1-C20 alkyl groups linear or branched, saturated or unsaturated, optionally containing heteroatoms, optionally substituted aryl groups, optionally substituted heteroaryl groups, optionally substituted cycloalkyl groups, optionally substituted heterocyclic groups, trialkyl- or triaryl-silyl groups, dialkyl- or diaryl-amino groups or dialkyl- or diaryl-phosphine groups, C1- C20,alkoxyl groups, preferably C1-Cio, linear or branched, saturated or unsaturated, optionally substituted aryloxy groups, optionally substituted thioalkoxyl or thioaryloxy groups, cyano groups, said cycle optionally containing heteroatoms such as, for example, oxygen, sulphur, nitrogen, silicon, phosphorus, selenium, preferably oxygen, nitrogen; provided that within the cycle or in any of its substitutions there is at least a double or a triple bond between two adjacent carbon atoms, and in the event that two or more double or triple bonds are present, said bonds may be conjugated or unconjugated, preferably unconjugated;
- n and m, equal to or different from each other, are an integer between 1 and 5000, preferably between 1 and 3000, provided that n + m is greater than or equal to 5;
comprising the following steps:
i) reacting at least one first epoxy compound having a general formula (II):
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in which R1 and R2 have the same meanings reported above;
with at least one second epoxy compound having a general formula (III):
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in which R3 and R4 have the same meanings reported above; and
carbon dioxide (CO2), in the presence of a catalytic system comprising at least one catalyst selected from complexes of a transition metal and, optionally, at least one co-catalyst selected from ionic compounds; wherein said at least one first epoxy compound having general formula (II) and said at least one second epoxy compound having general formula (III) are used in a molar ratio between 1:99 and 99:1, thus obtaining a terpolymer;
ii) reacting the terpolymer obtained in said step i) with at least one sulphur-containing compound having general formula (IV):
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in which Rs, R6 and R7, the same or different from each other, represent a hydrogen atom; or they are selected from C1-C20 alkyl groups, preferably CI-C12, linear or branched, saturated or unsaturated, optionally containing heteroatoms, optionally substituted aryl groups, optionally substituted heteroaryl groups, optionally substituted cycloalkyl groups, optionally substituted heterocyclic groups; provided that in said general formula (IV) at least one of between Rs, R6 and R7 differs from hydrogen and at least one of between Rs, R6 and R7, contains one of the following functional groups:-COOH, -COO-M*, -SO3H, -SO3-M*, -SO2H, -S02-M*, -OP03H2, -OPO32-M+2, -P03H2, -PO32-M'2, -OH, in which M* represents a monovalent inorganic cation such as, for example, cesium (Cs*), rubidium (Rb+), potassium (K+), lithium (Li+), sodium (Na*), copper (Cu*), silver (Ag*), ammonium (NH4*) or mixtures thereof, or M* represents a monovalent organic cation such as, for example, methylammonium (CH3NH3*), n-butylammonium (C4H12N+), ethanolammonium (C2H5ONH3*), diethanolammonium (C4HioO2NH2I), triethanolammonium (C6Hi503NH+), pyridinium (CSHSNH+), monohydroxypyridinium (CSH5ONH+), dihydroxypyridinium (CsHsNO2H+) or mixtures thereof; preferably M* is selected from between potassium (K+), sodium (Na*), ammonium (NH4*) or, more preferably, ammonium (NH4*).
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 1-23 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 pre-AIA the applicant regards as the invention.
Claim 1 recites the limitation "the preparation" and "the event"; Claims 1-3 recite the limitation "the other atoms"; Claim 4 recites the limitation "the atoms"; Claim 11 recites the limitation "the mixture"; Claims 19 and 21 recite the limitation "the vinyl groups". There are insufficient antecedent bases for these limitations in the claims.
Regarding Claims 1 and 3, the phrase "for example" renders the claim indefinite because it is unclear whether the limitation(s) following the phrase are part of the claimed invention. See MPEP § 2173.05(d). For the purposes of examination, the claim language of “for example” will be interpreted to mean “not required”.
Regarding Claims 1-3, 9, 17, and 20, the phrase "such as" renders the claim indefinite because it is unclear whether the limitations following the phrase are part of the claimed invention. See MPEP § 2173.05(d). For the purposes of examination, the claim language of “such as” will be interpreted to mean “not required”.
A broad range or limitation together with a narrow range or limitation that falls within the broad range or limitation (in the same claim) may be considered indefinite if the resulting claim does not clearly set forth the metes and bounds of the patent protection desired. See MPEP § 2173.05(c). In the present instance, Claim 10 recites said organic solvent is used in volume ratio with respect to the epoxy compounds is “between 0:100 and 99:1” which includes the broad recitation of no organic solvent. However, Claim 10 is dependent on Claim 9 which requires the presence of the organic solvent and is a narrower statement of the range. The claim(s) are considered indefinite because there is a question or doubt as to whether the feature introduced by such narrower language is (a) merely exemplary of the remainder of the claim, and therefore not required, or (b) a required feature of the claims. For the purposes of examination, the claim language of “preferably” will be interpreted to mean “not required”.
Claim 1 recites the broad recitation “C1-C30 alkyl groups”, and the claim also recites “preferably C1-C20” which is the narrower statement of the range/limitation. Similarly, Claims 1-3, 6, 8-10, 12-14, and 16-23 contain the “preferably” language. All instances of the word “preferably” are considered indefinite as set forth above. The Claims 1-3, 6, 8-10, 12-14, and 16-23 are thereby rejected.
Claims 10 and 12 recite “the epoxy compounds [i.e., said at least one epoxy compound having general formula (II) + said at least one second epoxy compound having general formula (III)] are used in a molar ratio” which is unclear. For purposes of examination, “the epoxy compounds [i.e., said at least one epoxy compound having general formula (II) + said at least one second epoxy compound having general formula (III)] are used in a molar ratio” of Claims 10 and 12 will be interpreted as “the at least one epoxy compound having general formula (II) + said at least one second epoxy compound having general formula (III)] are used in a molar ratio”.
Claim 23 is rejected as being indefinite because of the language “Use of a functionalized terpolymer” in the preamble. There are no positively recited steps in the claim thereby rendering the claim unclear because it is unknown how the polymer composition is being used.
Furthermore, Claims 2-23 are rejected for being dependent on rejected base Claim 1.
Claim Rejections - 35 USC § 101
35 U.S.C. 101 reads as follows:
Whoever invents or discovers any new and useful process, machine, manufacture, or composition of matter, or any new and useful improvement thereof, may obtain a patent therefor, subject to the conditions and requirements of this title.
Claim 23 is rejected under 35 U.S.C. 101 because the claimed invention is not supported by either a specific and substantial asserted utility or a well-established utility.
Claim 23 is rejected under 35 U.S.C. 101 because the claimed recitation of a use, without setting forth any steps involved in the process, results in an improper definition of a process, i.e., results in a claim which is not a proper process claim under 35 U.S.C. 101.
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 1, 5-11, 14-15, 17-22 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (CN107446122A; cited in the IDS submitted on 11/09/2023; English translation incorporated herein; hereafter as “Liu”).
For the purposes of examination, the claimed optional limitations will be interpreted to not be required.
Regarding Claims 1, 5-7, 15 and 19, Liu teaches a method for preparing a functionalized polycarbonate [Claim 1], corresponding to the process for the preparation of a functionalized terpolymer of Claim 1. The method comprising:
said polycarbonate having formula (I-2) [¶ 0043], corresponding to the functionalized terpolymer having general formula (I); wherein:
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R2 is a hydrogen [¶ 0045], thereby reading on R1, R3, R4, are hydrogen of Claim 1;
Q is a thiol compound, such as mercaptoacetic acid [¶ 0046, 0053], thereby reading on R2 is a C1-C30 alkyl group containing a heteroatom of Claim 1;
m = 0.05~1 and n = 0~0.95 [¶ 0050], which is equivalent to m ≥ 1 and n ≥ 0, which overlaps with n and m, equal to or different from each other, are an integer between 1 and 5000, and n + m is greater than or equal to 5 of Claim 1;
4-vinylepoxycyclohexane [¶ 0023], corresponding to the first epoxy having general formula (II) of Claim 1, and thereby reading on the 4-vinylepoxycyclohexane Claim 7;
propylene oxide[¶ 0023], corresponding to the second epoxy having general formula (III) of Claim 1, thereby reading on the C2-C20 alkylene oxide of Claim 5, and thereby reading on the propylene oxide of Claim 6;
carbon dioxide [¶ 0029], corresponding to the carbon dioxide of Claim 1;
SalenCo-Cl catalyst [¶ 0029], corresponding the transition metal catalyst of Claim 1;
copolymerizing carbon dioxide and epoxide in the presence of a catalyst to obtain polycarbonate [¶ 0029], corresponding to reacting at least epoxy compound and carbon dioxide in the presence of a catalytic system comprising a transition metal catalyst of Claim 1;
mercaptoacetic acid [¶ 0029, 0053], corresponding to sulphur-containing compound having general formula (IV) of Claim 1, and thereby reading on the mercaptoacetic acid of Claim 15;
wherein:
hydrogen read on R5, R6 are hydrogen of Claim 1;
-COOH reads on R7 is a C1-C20 alkyl group with a -COOH functional group of Claim 1; and
polycarbonate reacts with a thiol compound [¶ 0029], corresponding to reacting the terpolymer with at least one sulphur-containing compound of Claim 1.
However, Liu is silent to n and m, equal to or different from each other, are an integer between 1 and 5000, provided that n + m is greater than or equal to 5 of Claim 1; and first epoxy compound having general formula (II) and said at least one second epoxy compound having general formula (III) are used in a molar ratio between 1:99 and 99:1 of Claim 1; and said sulphur-containing compound used in a molar ratio of between 100:1 and 1:1 with respect to the vinyl groups present in the terpolymer of Claim 19.
Nevertheless, one of ordinary skill in the art at the time the invention was made would have considered the invention to have been obvious because the range taught by Liu for the n and m (m = 0.05~1 and n = 0~0.95) overlaps the instantly claimed range (n and m, equal to or different from each other, are an integer between 1 and 5000, and n + m is greater than or equal to 5) and is therefore considered to establish a prima facie case of obviousness. It would have been obvious to one of ordinary skill in the art to select any portion of the disclosed ranges including the instantly claimed ranges from the ranges disclosed in the prior art reference, MPEP 2144.05.
Furthermore, Liu teaches the molar ratio of epoxides need to be adjusted according to the desired final polycarbonate molecular weight distribution [¶ 0054] and the amount of epoxy is preferably optimized relative to the amount of catalyst and transition metal, and solvent [¶ 0072, 0075, 0078]. Liu also teaches the polycarbonate reacts with the thiol compound (which corresponds to the sulphur-containing compound) to undergo double bond-thiol click reaction, yielding a functionalized polycarbonate [¶ 0057]. Therefore, the amount and ratio of the epoxies and sulphur-containing compound can be optimized to reach the desired molecular weight distribution and the number of double bonds of the final polycarbonate product via a routine optimization. The case law has held that discovering an optimum value of a result effective variable involves only routine skill in the art. See MPEP 2144.05. Thus, it would have been obvious to one having ordinary skill in the art at the time of the invention was made to adjust the ratio of epoxies for the intended application via a routine optimization, thereby obtaining the present invention.
Regarding Claims 8-10, 14, 17, 20-22, Liu further teaches:
3,4-epoxy-1-butene [¶ 0060], thereby reading on the 3,4-epoxy-1-butene of Claim 8;
Toluene [¶ 0069], thereby reading on the toluene of Claims 9 and 17;
A 1:1 volume ratio of organic solvent to epoxy [¶ 0078], corresponding to a volume ratio of organic solvent to epoxy between 0:100 and 99:1 of Claim 10;
Carrying out the process at a temperature of 20-80˚C, at a pressure of 0.1-5MPa (which is equivalent to 1 to 50 atm) for 10-40 hours [¶ 0068], corresponding to a temperature of 20-250˚C, at a pressure of 1 to 100 atm for 30min to 36 hours of Claim 14, and thereby reading on a period of time between 10 hours and 36 hours of Claim 22;
azobisisobutyronitrile, a free radical initiator [Claim 10; ¶ 0082], thereby reading on the azobisisobutyronitrile of Claim 20.
Regarding Claim 11, however, Liu does not explicitly teach the mixture of the first epoxide and second epoxide works as a solvent.
Nevertheless, the ability for the epoxide mixture to work as a solvent is a function of its physical and chemical structure, and polarity. Since Liu teaches the same functionalized polycarbonate formed by the same method as required by the instant claim, as set forth in the rejection above, the functionalized polycarbonate of Liu would be expected to result in the same solubility as required by the instant claims. Case law has held that claiming of a new use, new function or unknown property which is expectedly present in the prior art does not necessarily make the claim patentable. In re Best, 562 F.2d 1252, 1254, 195 USPQ 430, 433 (CCPA 1977). The courts have stated that a chemical composition and its properties are inseparable. Therefore, if the prior art teaches the identical chemical structure, the properties applicant discloses and/or claims are necessarily present. In re Spada, 911 F.2d 705, 15 USPQ2d 1655, (Fed. Cir. 1990). See also In re Best, 562 F.2d 1252, 195 USPQ 430, (CCPA 1977). "Where the claimed and prior art products are identical or substantially identical in structure or composition, or are produced by identical or substantially identical processes, a prima facie case of either anticipation or obviousness has been established." Further, if it is the applicant's position that this would not be the case, evidence would need to be provided to support the applicant's position. In the alternative that the above disclosure is insufficient to anticipate the above listed claims, it would have nonetheless been obvious to the skilled artisan to produce the claimed functionalized polycarbonate properties, as the reference teaches each of the claimed ingredients (functionalized terpolymer, first epoxy, second epoxy, carbon dioxide, and sulphur-containing compound) for the same utility (polymerization) and for the same purpose (to producing a functionalized terpolymer).
Regarding Claim 18, Liu teaches 2 mL of tetrahydrofuran (THF) as an organic solvent to 0.5 g of polymer [¶ 0115], which is equivalent to a volume ratio of 5:1 (approx. density of polycarbonate = 1.2 g/mL; volume of polycarbonate = 0.5 g / 1.2 g/mL = 0.42 mL; ratio of solvent to polymer = 2 mL / 0.42 mL = 5:1), corresponding to said organic solvent is used in a volume ratio, with respect to said terpolymer, of between 1000:1 and 1:1 of Claim 18.
Regarding Claim 21, Liu teaches the polycarbonate reacts with a thiol compound in the presence of an initiator to undergo a double bond-thiol click reaction, yielding a functionalized polycarbonate [¶ 0057].
However, Liu does not explicitly teach said radical initiator is used in a molar ratio of between 1:2 and 1:0.01 with respect to the vinyl groups present in the terpolymer.
Nevertheless, the amount and ratio of the radical initiator can be optimized to reach the desired molar amount of vinyl groups in the terpolymer to yield a functionalized polycarbonate via a routine optimization. Greater amounts of initiator may result in a faster reaction with more vinyl groups in the functionalized polycarbonate. The case law has held that discovering an optimum value of a result effective variable involves only routine skill in the art. See MPEP 2144.05. Thus, it would have been obvious to one having ordinary skill in the art at the time of the invention was made to adjust the ratio of epoxies for the intended application via a routine optimization, thereby obtaining the present invention.
Claims 2, and 12-13 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (CN107446122A; cited in the IDS submitted on 11/09/2023; English translation incorporated herein; hereafter as “Liu”) in view of Biagini et al. (WO 2020/079573 A1; cited in the IDS submitted on 11/09/2023; hereafter as “Biagini ‘573”).
Regarding Claim 2, Liu teaches the method of preparation of a functionalized terpolymer, first epoxy, second epoxy, carbon dioxide, and sulphur-containing compound of Claim 1 as set forth above and incorporated herein by reference.
Liu further teaches:
SalenCo-Cl catalyst [¶ 0029], corresponding to the catalyst complex with a transition metal having general formula (V); wherein
cobalt reads on wherein M1 is cobalt of Claim 2;
hydrogens read on wherein R8 and R11 are each hydrogen of Claim 2;
substituted aryl groups read on wherein R9, R10, R12 and R13 are bonded together as to form a cycle containing 2 to 12 carbon atoms of Claim 2;
chloride anion reads on wherein Y represents a halide anion of Claim 2;
cyclohexane group reads on wherein Z represents a divalent organic radical having general formula (VII) of Claim 2, and wherein R16 and R17 are bonded together as to form a cycle containing 2 to 12 carbon atoms of Claim 2; and
hydrogens read on wherein R14 and R15 are each hydrogen of Claim 2.
However, Liu is silent to the co-catalyst of Claim 2.
Nevertheless, Biagini ‘573 teaches a process for preparing polycarbonate comprising a catalytic system copolymerizing an epoxy compound and carbon dioxide in the presence of a catalytic transition metal complex [Claim 1], comprising:
A co-catalyst selected from ionic compounds having general formula (V) (shown below) [Claim 1], corresponding to the co-catalyst selected from ionic compounds having general formula (IX);
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Wherein:
E represents a phosphorus [Claim 1], thereby reading on E represents phosphorus;
R13, R14, R15, R16, R17, R18, R19 and R20 each represent a hydrogen atom [Claim 1], thereby reading on R20, R21, R22, R23, R24, R25, R26 and R27 each represent a hydrogen atom;
W represents a halogen atom [Claim 1], thereby reading on W represents a halogen atom;
X- represents a halide anion [Claim 1], thereby reading on X- represents a halide anion;
a is an integer between 0 and 4 [Claim 1], corresponding to a is an integer between 0 and 4;
a is 4 [Claim 1], thereby reading on a is 4;
b is 0 [Claim 1], thereby reading on b is 0;
c is 0 [Claim 1], thereby reading on c is 0;
the sum of a + b + c is equal to 4, corresponding to the sum of a + b + c is equal to 4 and that at least either a or b is not 0;
n is an integer between 1 and 4 [Claim 1], corresponding to n is an integer between 1 and 4.
Regarding Claims 12-13, Biagini ‘573 further teaches:
said catalytic system and the epoxy compound are used in a molar ratio of 1:100 to 1:100000 [Claim 6], corresponding to said catalytic system and the epoxy compound are used in a molar ratio ranging from 1:100 to 1:100000 of Claim 12; and
said catalyst selected from complexes of a transition metal and said co-catalyst selected from ionic compounds are used in a molar ratio ranging from 100:1 to 1:100 [Claim 6], corresponding to said at least one catalyst selected from complexes of a transition metal and said at least one co-catalyst selected from ionic compounds are used in a molar ratio of between 100:1 to 1:100 of Claim 13.
Biagini ‘573 offers the motivation that said catalytic system comprising the catalytic transition metal complex and the co-catalyst allows the quantity of carbonate bonds in the polycarbonate chain to be modulated, with greater than 95% carbonate bonds in the chain [Page 23, ¶ 3]. Biagini ‘573 also offers the motivation that the polycarbonate obtained with said catalytic system is easily degradable and does not form residue in combustion [Page 23, ¶ 4].
Liu and Biagini ‘573 are considered to be analogous art as the claimed invention, as all are in the same field of methods of preparing polycarbonate comprising a catalytic system copolymerizing an epoxy compound and carbon dioxide in the presence of a catalytic transition metal complex.
Therefore, it would be obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use the co-catalyst of Biagini ‘573 with the process of Liu, with the motivation to form an easily degradable polymer, thereby arriving at the claimed invention.
Claim 3 is rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (CN107446122A; cited in the IDS submitted on 11/09/2023; English translation incorporated herein; hereafter as “Liu”) an in further view of Biagini et al. (WO 2019/092266 A1; cited in the IDS submitted on 11/09/2023; hereafter as “Biagini ‘266”).
Liu teaches the method of preparation of a functionalized terpolymer, first epoxy, second epoxy, carbon dioxide, and sulphur-containing compound of Claim 1 as set forth above and incorporated herein by reference.
Liu further teaches:
SalenCo-Cl catalyst [¶ 0029], corresponding to the catalyst complex with a transition metal having general formula (V); wherein
cobalt reads on wherein M1 is cobalt;
hydrogens read on wherein R8 and R11 are each hydrogen;
substituted aryl groups read on wherein R9, R10, R12 and R13 are bonded together as to form a cycle containing 2 to 12 carbon atoms;
chloride anion reads on wherein Y represents a halide anion;
cyclohexane group reads on wherein Z represents a divalent organic radical having general formula (VII) of Claim 2, and wherein R16 and R17 are bonded together as to form a cycle containing 2 to 12 carbon atoms; and
hydrogens read on wherein R14 and R15 are each hydrogen.
However, Liu is silent to the co-catalyst of Claim 3.
Nevertheless, Biagini ‘266 teaches a process for preparing polycarbonate comprising a catalytic system copolymerizing an epoxy compound and carbon dioxide in the presence of a catalytic transition metal complex [Claim 1], comprising:
A co-catalyst selected from ionic compounds having general formula (II) (shown below) [Claim 1], corresponding to the co-catalyst selected from ionic compounds having general formula (X);
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Wherein:
M represents a phosphorus [Claim 1], thereby reading on E represents phosphorus;
R1, R2, R3 and R4 each represent a hydrogen atom [Claim 1], thereby reading on R28, R29, R30, and R31, reach represent a hydrogen atom;
X- represents a halogen anion [Claim 1], thereby reading on X- represents a halide anion.
Biagini ‘266 offers the motivation that co-catalysts in the production of polycarbonate modify the activity and selectivity of the catalytic system, and determine the final properties of the obtained polycarbonate [Page 4, ¶ 3].
Liu and Biagini ‘266 are considered to be analogous art as the claimed invention, as all are in the same field of methods of preparing polycarbonate comprising a catalytic system copolymerizing an epoxy compound and carbon dioxide in the presence of a catalytic transition metal complex.
Therefore, it would be obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use the co-catalyst of Biagini ‘266 with the process of Liu, with the motivation to modify the final properties of the obtained polycarbonate, thereby arriving at the claimed invention.
Claim 4 is rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (CN107446122A; cited in the IDS submitted on 11/09/2023; English translation incorporated herein; hereafter as “Liu”) in view of Mang et al. (Copolymerization of CO2 and 1,2-Cyclohexene Oxide Using a CO2 -Soluble Chromium Porphyrin Catalyst, Macromolecules 2000, 33, 303-308; cited in the IDS submitted on 11/09/2023; hereafter as “Mang”), Biagini et al. (WO 2019/092266 A1; cited in the IDS submitted on 11/09/2023; hereafter as “Biagini ‘266”), and Biagini et al. (WO 2020/079573 A1; cited in the IDS submitted on 11/09/2023; hereafter as “Biagini ‘573”).
Liu teaches the method of preparation of a functionalized terpolymer, first epoxy, second epoxy, carbon dioxide, and sulphur-containing compound of Claim 1 as set forth above and incorporated herein by reference.
Liu teaches transition metal catalysts [¶ 0029], corresponding to the catalyst complex with a transition metal, as set forth above.
However, Liu is silent to a catalyst having general formula (XI) ; co-catalyst having general formula (X); and ionic compound having general formula (IX).
Regarding the catalyst having the general formula (XI), Mang teaches copolymerization of carbon dioxide and 1,2-cyclohexene oxide, an epoxy, using a chromium catalyst [Abstract], comprising:
Chromium porphyrin complex [Scheme 1] (shown below), corresponding to the transition metal catalyst complex having general formula (XI);
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wherein:
Cr(III) reads on M1 represents chromium;
Cl reads on Y1 represents a halide anion;
C6F5 reads on R32 represents a C1-C20 akyl group with heteroatoms;
Hydrogens read on R33 and R34 each represent a hydrogen;
Mang offers the motivation that said chromium porphyrin complex is soluble in both liquid and supercritical carbon dioxide at moderate pressures and temperatures [Page 304].
Regarding the co-catalyst having general formula (X), Biagini ‘266 teaches a process for preparing polycarbonate comprising a catalytic system copolymerizing an epoxy compound and carbon dioxide in the presence of a catalytic transition metal complex [Claim 1], comprising:
A co-catalyst selected from ionic compounds having general formula (II) (shown below) [Claim 1], corresponding to the co-catalyst selected from ionic compounds having general formula (X);
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Wherein:
M represents a phosphorus [Claim 1], thereby reading on E represents phosphorus;
R1, R2, R3 and R4 each represent a hydrogen atom [Claim 1], thereby reading on R28, R29, R30, and R31, reach represent a hydrogen atom;
X- represents a halogen anion [Claim 1], thereby reading on X- represents a halide anion.
Biagini ‘266 offers the motivation that co-catalysts in the production of polycarbonate modify the activity and selectivity of the catalytic system, and determine the final properties of the obtained polycarbonate [Page 4, ¶ 3].
Regarding the ionic compound having general formula (IX), Biagini ‘573 teaches a process for preparing polycarbonate comprising a catalytic system copolymerizing an epoxy compound and carbon dioxide in the presence of a catalytic transition metal complex [Claim 1], comprising:
A co-catalyst selected from ionic compounds having general formula (V) (shown below) [Claim 1], corresponding to the co-catalyst selected from ionic compounds having general formula (IX);
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Wherein:
E represents a phosphorus [Claim 1], thereby reading on E represents phosphorus;
R13, R14, R15, R16, R17, R18, R19 and R20 each represent a hydrogen atom [Claim 1], thereby reading on R20, R21, R22, R23, R24, R25, R26 and R27 each represent a hydrogen atom;
W represents a halogen atom [Claim 1], thereby reading on W represents a halogen atom;
X- represents a halide anion [Claim 1], thereby reading on X- represents a halide anion;
a is an integer between 0 and 4 [Claim 1], corresponding to a is an integer between 0 and 4;
a is 4 [Claim 1], thereby reading on a is 4;
b is 0 [Claim 1], thereby reading on b is 0;
c is 0 [Claim 1], thereby reading on c is 0;
the sum of a + b + c is equal to 4, corresponding to the sum of a + b + c is equal to 4 and that at least either a or b is not 0;
n is an integer between 1 and 4 [Claim 1], corresponding to n is an integer between 1 and 4.
Biagini ‘573 offers the motivation that said catalytic system comprising the catalytic transition metal complex and the co-catalyst allows the quantity of carbonate bonds in the polycarbonate chain to be modulated, with greater than 95% carbonate bonds in the chain [Page 23, ¶ 3]. Biagini ‘573 also offers the motivation that the polycarbonate obtained with said catalytic system is easily degradable and does not form residue in combustion [Page 23, ¶ 4].
Liu, Mang, Biagini ‘266, and Biagini ‘573 are considered to be analogous art as the claimed invention, as all are in the same field of methods of preparing polycarbonate comprising a catalytic system copolymerizing an epoxy compound and carbon dioxide in the presence of a catalytic transition metal complex.
Therefore, it would be obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use the catalyst of Mang, ionic compound of Biagini ‘573, ionic compound of Biagini ‘266 with the process of Liu, with the motivation to prepare the polycarbonate at moderate pressures and temperatures and to modify the final properties of the obtained easily degradable polycarbonate, thereby arriving at the claimed invention.
Claims 16 and 23 are rejected under 35 U.S.C. 103 as being unpatentable over Liu et al. (CN107446122A; cited in the IDS submitted on 11/09/2023; English translation incorporated herein; hereafter as “Liu”) in view of Nishioka et al. (WO 2020/153329 A1; hereafter as “Nishioka”).
Liu teaches the method of preparation of a functionalized terpolymer, first epoxy, second epoxy, carbon dioxide, and sulphur-containing compound of Claim 1 as set forth above and incorporated herein by reference.
However, Liu is silent to use the sulphur-containing compounds of Claim 16, and use of the functionalized terpolymer as an additive for cements of Claim 23.
Nevertheless, Nishioka teaches a technique for functionalizing polycarbonate comprising polymerizing epoxides and carbon dioxide in the presence of a metal catalyst [¶ 0057], free radical initiators such as azobis(isobutyronitrile) [¶ 0120], solvents such as toluene [¶ 0119] to obtain a polycarbonate.
Nishioka further teaches:
thioglycolic acid [¶ 0116], thereby reading on the thioglycolic acid of Claim 16; and
use of the functionalized polycarbonate as an adhesive composition [¶ 0132], corresponding to use of the functionalized terpolymer as an additive for cements of Claim 23.
Nishioka offers the motivation that the resulting functionalized polycarbonate exhibits excellent thermal decomposition [Abstract] and excellent adhesive effects [¶ 0132].
Liu and Nishioka are considered to be analogous art as the claimed invention, as all are in the same field of methods of preparing polycarbonate comprising a catalytic system copolymerizing an epoxy compound and carbon dioxide in the presence of a catalytic transition metal complex.
Therefore, it would be obvious to one of ordinary skill in the art before the effective filing date of the claimed invention to use thioglycolic acid of Nishioka with the process of Liu to produce an adhesive, with the motivation to prepare an excellent adhesive with excellent thermal decomposition properties, thereby arriving at the claimed invention.
Conclusion
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/DORIS LING/Examiner, Art Unit 1764
/ARRIE L REUTHER/Supervisory Primary Examiner, Art Unit 1764
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