EP4658705A1 - Polyetherimide and composition and article made therefrom - Google Patents

Abstract

A polyetherimide includes repeating units derived from a dianhydride selected from 4,4'- ((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(isobenzofuran-1, 3-dione); or 4,4'-([1,1'- biphenyl]-4,4'-diylbis(oxy))bis(isobenzofuran-1, 3-dione); a first diamine including 9,9-bis(4- aminophenyl)fiuorene; and a second diamine including di aminodiphenyl ether, 4,4'- diaminodiphenyl sulfone, meta-phenylene diamine, or para-phenylene diamine. The polyetherimide can exhibit a desirable combination of properties. Methods of making the polyetherimide and polymer compositions and articles including the polyetherimide are also disclosed.

Description

22SHPP0074-WO-PCT (SS240080PCT) POLYETHERIMIDE AND COMPOSITION AND ARTICLE MADE THEREFROM CROSS REFERENCE TO RELATED APPLICATION This application claims priority to European Patent Application No.23153988.3, filed on January 30, 2023, the contents of which are hereby incorporated by reference in their entirety. BACKGROUND [0001] Polyimides, and in particular polyetherimides (PEI), are high performance polymers having a glass transition temperature (Tg) of greater 180 °C. These polymers further have high strength, heat resistance, and modulus, and broad chemical resistance. Polyetherimides are widely used in applications as diverse as automotive and electrical/electronic applications since these compositions offer good mechanical and thermal properties. [0002] The use of known polyetherimides in some high temperature applications has been limited. For example, some polyetherimides have Tg values that are not sufficiently high to withstand a lead-free soldering process. Other polyetherimides having higher Tg values can often display high moisture uptake, reduced thermal stability, SO₂ outgassing, low dimensional stability, low IR transmission, and high viscosity which can be undesirable for some applications. [0003] Accordingly, there remains a continuing need in the art for new polyetherimides that exhibit improved heat performance (e.g., high Tg and high thermal stability) and good flow properties. It would be further advantageous to simultaneously retain most of the advantageous properties associated with known polyetherimides. SUMMARY [0004] A polyetherimide comprises repeating units derived from a dianhydride selected from 4,4'-((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(isobenzofuran-1,3-dione); or 4,4'- ([1,1'-biphenyl]-4,4'-diylbis(oxy))bis(isobenzofuran-1,3-dione); a first diamine comprising 9,9- bis(4-aminophenyl)fluorene; and a second diamine comprising diaminodiphenyl ether, 4,4’- diaminodiphenyl sulfone, meta-phenylene diamine, or para-phenylene diamine. [0005] Another aspect of the present disclosure is a polymer composition comprising the polyetherimide. [0006] Another aspect of the present disclosure is an article comprising the polyetherimide or the polymer composition. 22SHPP0074-WO-PCT (SS240080PCT) [0007] A method for the manufacture of the polyetherimide comprises combining the dianhydride and the diamine under conditions effective to provide the polyetherimide. [0008] The above described and other features are exemplified by the following detailed description. DETAILED DESCRIPTION [0009] Described herein is a polyetherimide including repeating units derived from a particular combination of monomers. The present inventors have unexpectedly found that the polyetherimide according to the present disclosure can exhibit a desirable combination of properties, for example high melt flow, good optical properties, and good thermal properties, as further described herein. [0010] Accordingly, an aspect of the present disclosure is a polyetherimide. The polyetherimide comprises repeating units derived from a dianhydride, a first diamine, and a second diamine. [0011] The dianhydride is selected from 4,4'-((propane-2,2-diylbis(4,1- phenylene))bis(oxy))bis(isobenzofuran-1,3-dione) or 4,4'-([1,1'-biphenyl]-4,4'- diylbis(oxy))bis(isobenzofuran-1,3-dione) shown as Formulas (I) and (II), respectively. [0012] In an aspect, the dianhydride is the 4,4'-((propane-2,2-diylbis(4,1- phenylene))bis(oxy))bis(isobenzofuran-1,3-dione) (i.e., the dianhydride according to Formula (I)). The dianhydride according to Formula (I) may also be referred to as “3,3’-BPADA” herein. [0013] In an aspect, the dianhydride is the 4,4'-([1,1'-biphenyl]-4,4'- diylbis(oxy))bis(isobenzofuran-1,3-dione) (i.e., the dianhydride according to Formula (II)). The dianhydride according to Formula (II) may also be referred to as “3,3’-BPoDA” herein. [0014] The poly(etherimide) can optionally further comprise additional repeating units derived from polymerization of a dianhydride different from the dianhydrides according to Formula (I) and Formula (II). The dianhydride different from the dianhydride according to Formula (I) and Formula (II) can be present in the poly(etherimide) in an amount of 0 to 2 weight percent, or 0 to 1.5 weight percent, or 0 to 1 weight percent, or 0 to 0.5 weight percent or 0 to 0.1 weight percent, each based on total moles of dianhydride. In an aspect, the 22SHPP0074-WO-PCT (SS240080PCT) polyetherimide does not comprise repeating units derived from any dianhydride other than the dianhydride according to Formula (I) or Formula (II). [0015] When present, the dianhydride different from the dianhydride according to Formula (I) or Formula (II) can be of the formula (III) or (IV) wherein T is -O- or a group of the formula -O-Z-O- wherein the divalent bonds of the -O- or the -O-Z-O- group are in the 3,3', 3,4', 4,3', or the 4,4' positions, and Z is an aromatic C_6-24 monocyclic or polycyclic group optionally substituted with 1 to 6 C_1-8 alkyl groups, 1-8 halogen atoms, or a combination thereof; and R¹ and R² are each independently a hydrogen, a C_1-8 alkyl group, a halogen, or a combination thereof, preferably hydrogen. Preferably, Z can be a group derived from a dihydroxy compound of the formula (V) wherein R^a, R^b, p and q are as defined above; c is 0 to 4; and X^a is -O-, -S-, -S(O)-, -SO2-, - C(O)-, or a C1-18 organic bridging group. In an aspect, the poly(etherimide) further comprises the second dianhydride of the formula (III), provided that the second dianhydride of the formula (III) is not the same as the dianhydride according to Formula (I) or Formula (II). In an aspect. the poly(etherimide) further comprises the second dianhydride of the formula (IV). In an aspect, the polyetherimide can exclude repeating units derived from formula (III), formula (IV), or both. [0016] The dianhydride is polymerized with a first diamine and a second diamine to provide the polyetherimide of the present disclosure. The first diamine comprises 9,9-bis(4- aminophenyl)fluorene, which may also be referred to as “BAF” herein and is shown in Formula (VI). [0017] The second diamine comprises diaminodiphenyl ether (also referred to herein as “DADE”), 4,4’-diaminodiphenyl sulfone (also referred to herein as “DDS”), meta-phenylene 22SHPP0074-WO-PCT (SS240080PCT) diamine (also referred to herein as “mPD”), or para-phenylene diamine (also referred to herein as “pPD”). DADE, DDS, mPD, and pPD are shown in Formulas (VII)-(X), respectively. [0018] In an aspect, the polyetherimide does not comprise repeating units derived from a fluorine substituted diamine. Stated another way, in some aspects the polyetherimide does not include any fluorine substituents along the polymer backbone. For example, the polyetherimide can exclude repeating units derived from a fluorine containing diamine such as bistrifluoromethylbenzidine (TFMB) (e.g., 2,2’- bistrifluoromethylbenzidine). Advantageously, polyetherimides excluding fluorine substituents can be desirable for regulatory reasons. For example, it can be desirable to provide a composition having less than 5000 ppm of fluorine, or less than 1000 ppm of fluorine, or less than 100 ppm of elemental fluorine. Furthermore, previous work has relied on inclusion of fluorine substituents to increase transparency of the material, however as shown below in the working examples, this is not necessary to achieve the desired optical properties for the compositions according to the present disclosure. [0019] In an aspect, the polyetherimide comprises repeating units derived from the first diamine comprising 9,9-bis(4-aminophenyl)fluorene and the second diamine comprising diaminodiphenyl ether. In an aspect, the polyetherimide comprises the repeating units derived from the first diamine comprising 9,9-bis(4-aminophenyl)fluorene and the second diamine comprising 4,4’-diaminodiphenyl sulfone. In an aspect, the polyetherimide comprises the repeating units derived from the first diamine comprising 9,9-bis(4-aminophenyl)fluorene and the second diamine comprising meta-phenylene diamine. In an aspect, the polyetherimide comprises the repeating units derived from the first diamine comprising 9,9-bis(4- aminophenyl)fluorene and the second diamine comprising para-phenylene diamine. [0020] In a specific aspect, the polyetherimide comprises repeating units derived from the dianhydride comprising 4,4'-((propane-2,2-diylbis(4,1- phenylene))bis(oxy))bis(isobenzofuran-1,3-dione), the first diamine comprising 9,9-bis(4- aminophenyl)fluorene, and the second diamine comprising 4,4’-diaminodiphenyl ether. [0021] In a specific aspect, the polyetherimide comprises repeating units derived from the dianhydride comprising 4,4'-((propane-2,2-diylbis(4,1- 22SHPP0074-WO-PCT (SS240080PCT) phenylene))bis(oxy))bis(isobenzofuran-1,3-dione), the first diamine comprising 9,9-bis(4- aminophenyl)fluorene, and the second diamine comprising 4,4’-diaminodiphenyl sulfone. [0022] In a specific aspect, the polyetherimide comprises repeating units derived from the dianhydride comprising 4,4'-([1,1'-biphenyl]-4,4'-diylbis(oxy))bis(isobenzofuran-1,3-dione), the first diamine comprising 9,9-bis(4-aminophenyl)fluorene, and the second diamine comprising diaminodiphenyl ether. [0023] In a specific aspect, the polyetherimide comprises repeating units derived from the dianhydride comprising 4,4'-((propane-2,2-diylbis(4,1- phenylene))bis(oxy))bis(isobenzofuran-1,3-dione), the first diamine comprising 9,9-bis(4- aminophenyl)fluorene, and the second diamine comprising meta-phenylene diamine. [0024] In a specific aspect, the polyetherimide comprises repeating units derived from the dianhydride comprising 4,4'-((propane-2,2-diylbis(4,1- phenylene))bis(oxy))bis(isobenzofuran-1,3-dione), the first diamine comprising 9,9-bis(4- aminophenyl)fluorene, and the second diamine comprising para-phenylene diamine. [0025] In an aspect, the first diamine can be present in an amount of 10 mole percent to 98 mole percent, based on the total moles of the first diamine and the second diamine. Within this range, the first diamine comprising 9,9-bis(4-aminophenyl)fluorene can be present in an amount of at least 20 mole percent, or at least 30 mole percent, or at least 40 mole percent, or at least 50 mole percent, or at least 60 mole percent, or at least 70 mole percent, or at least 80 mole percent, each based on the total moles of the first diamine and the second diamine. Also within this range, the first diamine comprising 9,9-bis(4-aminophenyl)fluorene can be present in an amount of at most 97 mole percent, or at most 95 mole percent, or at most 90 mole percent, or at most 80 mole percent, or at most 70 mole percent, or at most 60 mole percent, or at most 50 mole percent, or at most 40 mole percent, or at most 30 mole percent, or at most 20 mole percent, each based on the total moles of the first diamine and the second diamine. [0026] The second diamine can be present in a complementary amount such the total the total moles of the first diamine and the second diamine total 100 mole percent. For example, the second diamine can be present in an amount of 2 mole percent to 90 mole percent, based on the total moles of the first diamine and the second diamine. Within this range, the second diamine can be present in an amount of at least 3 mole percent, or at least 5 mole percent, or at least 10 mole percent, or at least 20 mole percent, or at least 30 mole percent, or at least 40 mole percent, or at least 50 mole percent, or at least 60 mole percent, or at least 70 mole percent, or at least 80 mole percent, each based on the total moles of the first diamine and the second diamine. Also within this range, the second diamine can be present in an amount of at most 80 mole percent, or 22SHPP0074-WO-PCT (SS240080PCT) at most 70 mole percent, or at most 60 mole percent, or at most 50 mole percent, or at most 40 mole percent, or at most 30 mole percent, or at most 20 mole percent, each based on the total moles of the first diamine and the second diamine. [0027] In a specific aspect, the first diamine can be present in an amount of 60 mole percent to 98 mole percent, preferably 65 mole percent to 75 mole percent, or 75 mole percent to 85 mole percent, and the second diamine can be present in an amount of 2 mole percent to 40 mole percent, preferably 25 mole percent to 35 mole percent, or 15 mole percent to 25 mole percent, each based on the total moles of the first diamine and the second diamine. [0028] The polyetherimide can optionally further comprise at least one chain end derived from a chain stopper (also referred to as an endcapping agent). Chain stoppers can be employed during the polymerization reaction. The chain stopper limits molecular weight growth rate and thus can be used to control molecular weight in the polyetherimide. Exemplary chain stoppers include certain mono amines (for example aniline), mono anhydrides (for example phthalic anhydride), mono-phenolic compounds and the like. In an aspect, the chain stopper can preferably be a monoamine chain stopper or a monoanhydride chain stopper, more preferably aniline or phthalic anhydride. It should be understood however that the polyetherimide disclosed herein can be produced having any desired weight average molecular weight (Mw) with any end cap. Chain stoppers can be present, for example, in an amount of 1 mole percent to 10 mole percent, based on the total moles of dianhydride, diamine, and chain stopper. [0029] The polyetherimide of the present disclosure can have a weight average molecular weight of 30,000 g/mol to 65,000 g/mol. Within this range, the weight average molecular weight can be, for example, 35,000 g/mol to 60,000 g/mol, or 35,000 g/mol to 55,000 g/mol, or 35,000 g/mol to 50,000 g/mol, or 35,000 g/mol to 45,000 g/mol. Molecular weight can be determined using gel permeation chromatography (GPC) relative to polystyrene standards, eluting with dichloromethane. [0030] The polyetherimide of the present disclose can exhibit one or more advantageous properties. For example, the polyetherimide can exhibit a glass transition temperature of greater than 275°C, for example greater than 275 °C to 290 °C, as determined by differential scanning calorimetry. In an aspect, the polyetherimide can exhibit a melt flow rate of greater than 7 g/10 min, as determined at 367 °C under a 6.7 kg load. The polyetherimide can be transparent. For example, the polyetherimide can exhibit a percent transmission of at least 80% at 850 nm. The polyetherimide can exhibit a combination of the foregoing properties. For example, the polyetherimide can exhibit a melt flow rate of greater than 7 g/10 min, as determined at 367 °C under a 6.7 kg load and a transmission of at least 80% at 850 nm. In an aspect, the 22SHPP0074-WO-PCT (SS240080PCT) polyetherimide can exhibit a glass transition temperature of greater than 275 °C and a melt flow rate of greater than 7 g/10 min, as determined at 367°C under a 6.7 kg load. In an aspect, the polyetherimide can exhibit a glass transition temperature of greater than 275 °C and a transmission of at least 80% at 850 nm. In an aspect, the polyetherimide can exhibit a glass transition temperature of greater than 275 °C and a melt flow rate of greater than 7 g/10 min, as determined at 367 °C under a 6.7 kg load and a transmission of at least 80% at 850 nm. In an aspect, the polyetherimide can exhibit a yellowness index of less than 125. In an aspect, the polyetherimide can exhibit a glass transition temperature of greater than 275 °C, a melt flow rate of greater than 7 g/10 min, as determined at 367°C under a 6.7 kg load, and a yellowness index of less than 125. [0031] In a specific aspect, the polyetherimide comprises, consists essentially of, or consists of repeating units derived from 4,4'-((propane-2,2-diylbis(4,1- phenylene))bis(oxy))bis(isobenzofuran-1,3-dione), a first diamine that is 9,9-bis(4- aminophenyl)fluorene and a second diamine that is diaminodiphenyl ether. The polyetherimide can exhibit a melt flow rate of greater than 9 g/10 min, as determined at 367 °C under a 6.7 kg load; and a transmission of at least 80% at 850 nm. The polyetherimide can optionally exhibit a viscosity of greater than 200 Pa-s, as determined according to ASTM D3835 at 400 °C and 5000 s^-1. The polyetherimide can optionally exhibit a glass transition temperature of greater than 275°C, as determined by differential scanning calorimetry. The polyetherimide can optionally exhibit a yellowness index of less than 125. [0032] A method of making the polyetherimide represents another aspect of the present disclosure. The method of making the polyetherimide composition contacting the dianhydride, the first diamine and the second diamine under conditions effective to provide the polyetherimide. Conditions effective to provide the polyetherimide can include a temperature of 170 °C to 380 °C, and a solids content of 1 weight percent to 50 weight percent, preferably 20 weight percent to 40 weight percent, more preferably 25 weight percent to 35 weight percent. Polymerizations can be carried out for 2 hours to 24 hours, preferably 3 hours to 16 hours. The polymerization can be conducted at reduced, atmospheric, or high pressure. In an aspect, the method can optionally further comprise devolatilizing the polyetherimide at 360 °C to 390 °C for 1 minute to 30 minutes. Contacting the dianhydride and the first and second diamines can be in the presence of a solvent. Exemplary solvents can include ortho-dichlorobenzene, para- dichlorobenzene, meta-dichlorobenzene, meta-cresol, para-cresol, ortho-cresol, N- methylpyrrolidone, veratrole, chlorobenzene, xylene, 1,2,4-trichlorobenzene, 1,3,4- trichlorobenzene, ethyl benzoate, triglyme, benzonitrile, 3-nitrotoluene, 2-nitrotoluene, 1- 22SHPP0074-WO-PCT (SS240080PCT) nitrotoluene, 1,3-dimethyl-2-imidazolidinone, dimethyl acetamide, diphenyl ether, phenetole, sulfolane, or a combination thereof. In an aspect, the solvent comprises ortho-dichlorobenzene. [0033] The polyetherimide of the present disclosure can be useful in forming polymer compositions. A polymer composition comprising the polyetherimide represents another aspect of the present disclosure. The polymer composition can optionally comprise one or more thermoplastic polymers other than the polyetherimide. Such polymer compositions can include, for example, 1 weight percent to 99 weight of the polyetherimide according to the present disclosure and 1 weight percent to 99 weight percent of the second polymer, or 10 weight percent to 90 weight percent of the polyetherimide and 10 weight percent to 90 weight percent of the second polymer. [0034] Illustrative examples of second polymers include, but are not limited to, a polyacetal, poly(C_1-6 alkyl)acrylate, polyacrylamide, polyacrylonitrile, polyamide, polyamideimide, polyanhydride, polyarylene ether, polyarylene ether ketone, polyarylene ketone, polyarylene sulfide, polyarylene sulfone, polybenzothiazole, polybenzoxazole, polybenzimidazole, polycarbonate, polyester, poly(C_1-6 alkyl)methacrylate, polymethacrylamide, cyclic olefin polymer, polyolefin, polyoxadiazole, polyoxymethylene, polyphthalide, polysilazane, polysiloxane, polystyrene, polysulfide, polysulfonamide, polysulfonate, polythioester, polytriazine, polyurea, polyurethane, vinyl polymer, or a combination thereof. [0035] The polymer composition can include various additives ordinarily incorporated into compositions of these types, with the proviso that any additive is selected so as to not significantly adversely affect the desired properties of the composition. Exemplary additives include antioxidants, thermal stabilizers, light stabilizers, ultraviolet light (UV) absorbing additives, quenchers, plasticizers, lubricants, mold release agents, antistatic agents, visual effect additives such as dyes, pigments, and light effect additives, flame resistances, anti-drip agents, and radiation stabilizers. Particulate fillers and reinforcing fillers can also be present, and include mineral fillers, flaked fillers, carbon nanotubes, exfoliated nanoclays, carbon nanowires, carbon nanospheres, carbon-metal nanospheres, carbon nanorods, carbon-metal nanorods, nanoparticles, insoluble polymers, glass fibers, carbon fibers, glass-carbon fibers, talc including fibrous, modular, needle shaped, and lamellar talc, graphite, fibrillated fluoropolymers, polymer fibers and filaments, woven fibers, metal particles, inorganic fibers, single crystal fibers or “whiskers”, or the like. Combinations of additives can be used. The foregoing additives can be present individually in an amount from 0.005 weight percent to 10 weight percent, or combined in an amount from 0.005 weight percent to 20 weight percent, preferably 0.01 weight percent to 10 wt%, based on the total weight of the composition. 22SHPP0074-WO-PCT (SS240080PCT) [0036] Also provided herein are articles that include the polyetherimide or the polymer composition comprising the polyetherimide. The polyetherimide can be formed into articles using any suitable technique, for example, melt-processing techniques. Melt-molding methods can include injection molding, extrusion molding, blow molding, rotational molding, coining, and injection blow molding. For example, the melt molding method can be injection molding. In some embodiments, extrusion molding can be particularly suitable for the polyetherimides of the present disclosure. The polyetherimide can be formed into sheets or films by casting, blowing, or extruding. These can be further thermoformed into articles and structures that can be oriented from the melt or at a later stage in the processing of the compositions. The polyetherimide can be over-molded onto an article made from a different material or by a different process. The articles can also be formed using techniques such as compression molding or ram extruding. The articles can be further formed into other shapes by machining. Exemplary articles include a fiber, a film, a sheet, a foam, a filament, a molded article, an extruded article, or a powder. The properties of the polyetherimide of the present disclosure can be particularly suitable for forming thin-walled molded articles. In an aspect, the article can be an extruded film or an extruded sheet. The polyetherimide of the present disclosure can also be particularly suitable for use in optoelectronic applications. In particular, the polyetherimide can be used for optoelectronic articles such as transmitters, receivers, connectors, lenses, waveguides, and the like. [0037] The polyetherimide of the present disclosure is further illustrated by the following non-limiting examples. EXAMPLES [0038] Materials for the present examples are described in Table 1. No material used in the following examples was identified as having any fluorine-containing impurities as received. Table 1 Component Description 3,3’-BPADA 4,4'-((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(isobenzofuran-1,3-dione), CAS Reg. No.: 52256-80-1 4,4’-BPADA 4,4^-(4,4^-Isopropylidenediphenoxy)bis(phthalic anhydride), CAS Reg. No.: 38103-06-9 3,3’-BPoDA 4,4'-([1,1'-biphenyl]-4,4'-diylbis(oxy))bis(isobenzofuran-1,3-dione), CAS Reg. No.: 53303-54-1 BPDA Biphenyl dianhydride, CAS Reg. No.: 2420-87-3 BAF 9,9-Bis(4-aminophenyl)fluorene, CAS Reg. No.: 15499-84-0 DDS 4,4’-Diaminodiphenyl sulfone, CAS Reg. No.80-08-8 DADE Diaminodiphenyl ether, CAS Reg. No.: 101-80-4 mPD Meta-phenylene diamine, CAS Reg. No.: 108-45-2 pPD Para-phenylene diamine, CAS Reg. No.: 106-50-3 TFMB 2,2’-Bistrifluoromethylbenzidine, CAS Reg. No.: 341-58-2 PA Phthalic anhydride, CAS Reg. No.: 85-44-9 22SHPP0074-WO-PCT (SS240080PCT) [0039] Polymers of the present examples were prepared according to the following general procedure. A reactor was charged with the desired amount of each monomer, followed by o-dichlorobenzene to provide a solids content of 30%. The contents of the reactor were stirred and heated to a temperature of 190 °C under nitrogen. The reaction mixture was heated under reflux for five hours. Reaction progress was monitored by analyzing molecular weight using gel permeation chromatography (GPC) over time. Once the desired molecular weight was obtained, solvent was removed from the reactor. Molten polymer was isolated by passing through an extruder to a water-cooled pelletizer. [0040] The resulting polymers were characterized according to the following tests and test methods. [0041] Molecular weight was determined by gel permeation chromatography in dichloromethane relative to polystyrene standards. Samples were dissolved in either dichloromethane or a 50:50 mixture of hexafluoroisopropanol and dichloromethane (HFIP/DCM) when dichloromethane alone was inadequate for full dissolution. [0042] Glass transition temperature (Tg) was determined under nitrogen using differential scanning calorimetry (DSC) according to ASTM D3418. The test was performed using a DSC Q2000 DSC instrument by heating from -10 °C to 300 ^oC at a rate of 20 ^oC/min, and Tg values were determined from the second heat cycle via inflection point. [0043] Melt flow rate (MFR) was determined at a temperature of 367 °C under a 6.7 kg load according to ASTM D1238. [0044] Viscosity change is a measurement of the change in viscosity of the polymer after being maintained at a specified elevated temperature for a specified time. Viscosity change as described herein is the change in melt viscosity after being held at 400 ºC for 30 minutes in a parallel plate rheometer. Samples were run in the parallel plate at 6.28 rad/s, with a strain of 5% for 0 to 1800 seconds. [0045] IR transmission at 550 nm, 850 nm, 1150 nm, and 1310 nm was determined in accordance with ASTM D1003, using injection molded 1 mm thickness plaques. [0046] Notched Izod Impact (NII) strength was determined according to ASTM D256 using a 5.5 J pendulum and at 23 °C. [0047] Thermal Gravimetric Analysis (TGA) measurements were performed with a TA Q800 TGA. The samples were heated from 40 °C to 800 °C, under nitrogen or air, with a heating rate of 20 °C/min. The onset temperature is an extrapolated onset temperature as 22SHPP0074-WO-PCT (SS240080PCT) measured by the intersection of tangents according to ISO 11358-1. Weight loss percent is calculated from the initial mass and mass at 800 °C. [0048] Capillary rheometry (viscosity) was determined at 400 °C at 5000 s^-1 according to ASTM D3835. Heat deflection temperature (HDT) was determined at 1.82 MPa according to ASTM D648. Tensile properties were characterized according to ASTM D638. Flexural properties were characterized according to ASTM D790. Yellowness index (YI) was characterized according to ASTM D1925. A solution yellowness index can be taken by the same method, except the polymer is dissolved in methylene chloride at a polymer concentration of 3.5 wt%, then measured to yellowness under the same ASTM standard. The materials were also visually analyzed by eye in sunlight to assess the basic color of the material. [0049] Film integrity was measured by forming a thin film (~0.05 mm) from isolated solids on a hydraulic press which could be set to a temperature of 380 °C. Samples were pressed until no voids remained across a 4 mm line. Samples were then folded in half in the void free section, forming a crease at the folded edge. A sample film which remained intact without cracking at the folded edge would be considered to have maintained integrity (indicated as “yes” in the following Tables), while samples which were unable to fold or formed cracks were considered to have failed (indicated as “no” in the following Tables). A thermoplastic material with a viable viscosity should be formable when pressed at these conditions, which are similar to the temperature of an injection molding machine. [0050] Polymer composition and properties are summarized in Table 2. The amount of each component is given in mole percent (mol%). Table 2a Component Unit CE1 E1 E2 E3 E4 E5 E6 E7 CE2 CE3 3,3’BPADA mol% 47 46.8 46.4 48.3 47 47 46.8 47.1 47 4,4’BPADA mol% 47 3,3’-BPoDA mol% BPDA mol% BAF mol% 39 39 39.4 29 29 26.8 26.6 49 40 DDS mol% 50 21.5 22.3 DADE mol% 9.8 9.7 9.8 19 10 mPD mol% 19 pPD mol% TFMB mol% PA mol% 3 4.4 4.9 2.5 5 5 4.9 4 4 3 Properties Mw kg/mol 40 34.1 40 60.7 60.8 66.3 39 51.4 32.7 52.9 T_g ^oC 265 280 283 289 272 273 278 283 286 274 Melt Flow Rate g/10 m_in ^{9 22 11 1.2 - - 13 4 11 -} Viscosity Pa·sec 671 201 662 2,688 1,204 2,030 661 2,640 202 2,908 Viscosity Change % 37 -40 -21 -22 -29 -59 36 -27 -43 -30 IR Trans. % 78; 84 - 84; 79 - - - - 79; 82 - - 22SHPP0074-WO-PCT (SS240080PCT) (850nm; 1150nm) NII J/m 52 - 35 - - - - 67 - - TGA (air) ^oC - 536 533 532 530 528 535 532 531 551 TGA (N2) ^oC - 541 534 534 532 530 536 536 533 552 ^{Material appear. Color} _{Amber Yellow Yellow Yellow Yellow Yellow Yellow Yellow Yellow Y} ^L eⁱ l^g l_o ^h w^t Film Integrity Yes/no Yes No Yes Yes Yes Yes No Yes No Yes Solution Yellowness - - 35 - - - - - - - Index “-” means no data generated Table 2b Component Unit CE4 CE5 CE6 E8 E9 E10 E11 CE7 CE8 3,3’BPADA mol% 47 47 4,4’BPADA mol% 47 46.6 45.6 3,3’-BPoDA mol% 44.1 44.7 46 BPDA mol% 47 BAF mol% 40 48.1 48.4 16.8 16.8 17 40 40 38 DDS mol% DADE mol% 31.2 31.3 31.5 10 9.1 mPD mol% 10 pPD mol% 10 TFMB mol% 2.9 PA mol% 3 7.3 6 7.9 7.2 5.5 4.7 3.4 Properties Mw kg/mol 52.1 28.2 34.7 31.1 34.4 42.1 39.9 45.2 Tg ^oC 272 281 285 277 281 289 277 282 Melt Flow Rate g/10 - ^{7.3 2.1 17 7.} - - - m_in ^{1 1.2} Viscosity Pa·sec 4,862 547 1,508 211 450 1,175 255 - 214 Viscosity Change % -30 -5 -11 -9.8 -26 36 70 - -51 IR Trans. (850nm; % _{- - 85; 77 - 77} ^{- - -} 1150nm) _{; 76 -} NII J/m - - 57 - 84 - - - - TGA (air) ^oC 552 553 550 557 566 562 534 - 539 TGA (N2) ^oC 549 550 552 557 551 563 537 - 538 Material appear. Color Light Light Light Yellow - Yellow Yellow Yellow _Yellow ^{Amber Amber Amber} Thin Film Creas. Yes/no Yes No Yes No Yes Yes Yes No* Yes Solution - - 42 Yellowness Index - - - - - - “-” means no data generated “*” means a film could not be formed for testing [0051] Desired properties include a high Tg (e.g., greater than 275 °C), good melt flow rate (e.g., greater than 7 g/10 min), and good IR transmittance. From the data in Table 2, it can be seen that the polymers according to Examples 1-3, and 6-11 each meet the desired Tg. The polymers according to Examples 1, 2, 6, and 8-9 each meet the desired MFR. Examples 2, 7, and 9 each possess good IR transmittance at both 850 nm and 1150 nm. In some instances, particularly for examples wherein high molecular weight polymers were achieved, molding was attempted but unsuccessful (i.e., the composition could not be molded). In such cases, property testing which require a molded sample (e.g., IR transmission, NII) did not result in any data 22SHPP0074-WO-PCT (SS240080PCT) being generated. In contrast, comparative examples were observed to be deficient in at least one desired property. Comparative example 7 illustrates that using BPDA as the anhydride component did not provide the desired properties. Comparative example 8 shows that the addition of a fluorine containing component did not improve the transparency of the resulting composition. Comparative example 8 has 8,100 ppm (0.81 weight percent) elemental fluorine intentionally added from the addition of TFMB into the backbone. Exact fluorine amounts could be determined by ion chromatography. [0052] It would be especially advantageous to provide a polymer composition having a combination of the aforementioned properties. From the data in Table 2, it can be seen that the polymer composition according to Example 2 can advantageously provide a Tg of 283 °C, a MFR of 11 g/10 minutes, and IR transmittance of 84% at 850 nm and 79% at 1150 nm. [0053] Based on the data in Table 2, polymers based on 3,3’-BPADA/BAF/DADE (e.g., polymers according to examples 1-3) and 3,3’-BPoDA/BAF/DADE (e.g., polymers according to examples 8-10) were selected for further characterization. Blends of different molecular weight polymers were also extruded, molded and tested. Compositions and properties are summarized in Table 3 below. Table 3 Composition Unit E12 E13 E14 E15 E16 E17 E18 E1 wt% 70 60 E2 wt% 80 100 E3 wt% 30 40 20 E9 wt% 100 80 E10 wt% 20 25 E8 wt% 75 Properties Tg °C 281 281 284 283 282 283 281 MFR g/10 m_in ^{11.4 8.8 6.9 9.6 6.2 5.3 9.7} NII J/m 35 36 34 34 66 84 59 Viscosity Pa-s 137 156 182 158 224 - 173 HDT °C 254 256 257 256 248 - 248 Tens. Mod. MPa 2840 2860 2910 2880 2600 2680 2900 Tens. Stress @ ^MPa brk _{70 73 87 86 57 72 72} Tens. Elong. ^% @ brk _{2.8 3.1 3.9 4.1 2.5 3.7 3.3} Flex. Mod. MPa 3050 3030 2980 2990 2940 2860 2830 Flex. Stress @ ^MPa yld _{160 166 169 166 134 - 143} Flex. Stress @ ^MPa brk _{155 165 168 166 134 - 143} YI 119 123 - - 168 144 - [0054] Table 4 shows optical properties for a molded sample of the polymer according to Example 2 as well as a blend of the polymers according to Examples 10 and 8 in a 1:3 weight 22SHPP0074-WO-PCT (SS240080PCT) ratio (referred to as Example 18 in Table 3). For comparison, the optical properties of a commercially available polyetherimide (obtained as ULTEM^TM 1010 resin from SABIC) are also shown in Table 4. Percent transmission was recorded at a thickness of 1 mm for Example 2 and the Example E18 (E9/E7 blend), and at 3.2 mm for ULTEM^TM 1010 resin. The refractive index (RI) of each sample is also provided in Table 4. As shown in Table 4, the refractive index for E2 is similar to ULTEM^TM 1010 resin datasheet value. The optical properties summarized in Table 4 indicate that the polymers disclosed herein may be particularly well suited for optical applications. Table 4 Wavelength E2 E17 ULTEM^TM 1010 % transmission, 62.1% 40.9% 79% 550 nm % transmission, 83.9% 77.6% 86.5% 850 nm % transmission, 79.3% 77.5% 85.1% 1150 nm % transmission, 86% 83.3% 87.5% 1310 nm RI, 850 nm 1.639 1.658 1.639 [0055] Table 5 shows the results of optical property testing for the polymer according to the composition of Example 2. Table 5 Optical Properties Units Values YI @ 0.04” 77 ( 1 mm, 39 mils) YI @ 0.08” 103 ( 2 mm, 78 mils) YI @ 0.125” 117 ( 3.2 mm, 125 mils) Transmittance @ 0.04” % 78 (1 mm, 39 mils) Transmittance @ 0.08” % 66 (2 mm, 78 mils) Transmittance @ 0.125” % 57 (3.2 mm, 125 mils) [0056] This disclosure further encompasses the following aspects. [0057] Aspect 1: A polyetherimide comprising repeating units derived from a dianhydride selected from 4,4'-((propane-2,2-diylbis(4,1- phenylene))bis(oxy))bis(isobenzofuran-1,3-dione); or 4,4'-([1,1'-biphenyl]-4,4'- diylbis(oxy))bis(isobenzofuran-1,3-dione); a first diamine comprising 9,9-bis(4- aminophenyl)fluorene; and a second diamine comprising diaminodiphenyl ether, 4,4’- diaminodiphenyl sulfone, meta-phenylene diamine, or para-phenylene diamine. 22SHPP0074-WO-PCT (SS240080PCT) [0058] Aspect 2: The polyetherimide of aspect 1, wherein the dianhydride is 4,4'- ((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(isobenzofuran-1,3-dione). [0059] Aspect 3: The polyetherimide of aspect 1 or 2, wherein the dianhydride is 4,4'- ([1,1'-biphenyl]-4,4'-diylbis(oxy))bis(isobenzofuran-1,3-dione). [0060] Aspect 4: The polyetherimide of aspect 2 or 3, wherein the first diamine is 9,9- bis(4-aminophenyl)fluorene and the second diamine is 4,4’-diaminodiphenyl ether. [0061] Aspect 5: The polyetherimide of aspect 2, wherein the first diamine is 9,9-bis(4- aminophenyl)fluorene and the second diamine is 4,4’-diaminodiphenyl sulfone. [0062] Aspect 6: The polyetherimide of any of aspects 1 to 5, wherein the polyetherimide has a weight average molecular weight of 30,000 g/mol to 65,000 g/mol, preferably 35,000 g/mol to 45,000 g/mol, as determined by gel permeation chromatography in dichloromethane relative to polystyrene standards. [0063] Aspect 7: The polyetherimide of any of aspects 1 to 6, wherein the polyetherimide exhibits a glass transition temperature of greater than 275°C, as determined by differential scanning calorimetry. [0064] Aspect 8: The polyetherimide of any of aspects 1 to 7, wherein the polyetherimide exhibits one or more of: a melt flow rate of greater than 7 g/10 min, as determined at 367 °C under a 6.7 kg load; or a transmission of at least 80% at 850 nm; or a yellowness index of less than 125, as determined according to ASTM D1925; or less than 5000 ppm, or less than 1000 ppm, or less than 100 ppm of elemental fluorine, as determined using combustion ion chromatography. [0065] Aspect 9: The polyetherimide of aspect 1, wherein the dianhydride is 4,4'- ((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(isobenzofuran-1,3-dione), the first diamine is 9,9-bis(4-aminophenyl)fluorene, and the second diamine is diaminodiphenyl ether; wherein the polyetherimide has a weight average molecular weight of 35,000 g/mol to 45,000 g/mol; and wherein the polyetherimide exhibits: a viscosity of greater than 200 Pa-s, as determined according to ASTM D3835 at 400 °C and 5000 s^-1; and a melt flow rate of greater than 9 g/10 min, as determined at 367°C under a 6.7 kg load; and a transmission of at least 80% at 850 nm. [0066] Aspect 10: The polyetherimide of aspect 9, wherein the polyetherimide exhibits a glass transition temperature of greater than 275 °C, preferably greater than 275 °C to 290 °C, as determined by differential scanning calorimetry. [0067] Aspect 11: The polyetherimide of any of claims 1 to 10, wherein the first diamine is present in an amount of 60 mole percent to 98 mole percent, and the second diamine 22SHPP0074-WO-PCT (SS240080PCT) is present in an amount of 2 mole percent to 40 mole percent, each based on the total moles of the first diamine and the second diamine. [0068] Aspect 12: A polymer composition comprising the polyetherimide of any of aspects 1 to 11. [0069] Aspect 12: An article comprising the polyetherimide of any of aspects 1 to 11 or the polymer composition of aspect 12. [0070] Aspect 13: The article of aspect 12, wherein the article is an optical article, preferably a lens or an optoelectronic component. [0071] Aspect 14: A method for the manufacture of the polyetherimide of any of aspects 1 to 10, the method comprising: combining the dianhydride, the first diamine, and the second diamine under conditions effective to provide the polyetherimide. [0072] The compositions, methods, and articles can alternatively comprise, consist of, or consist essentially of, any appropriate materials, steps, or components herein disclosed. The compositions, methods, and articles can additionally, or alternatively, be formulated so as to be devoid, or substantially free, of any materials (or species), steps, or components, that are otherwise not necessary to the achievement of the function or objectives of the compositions, methods, and articles. [0073] All ranges disclosed herein are inclusive of the endpoints, and the endpoints are independently combinable with each other. “Combinations” is inclusive of blends, mixtures, alloys, reaction products, and the like. The terms “first,” “second,” and the like, do not denote any order, quantity, or importance, but rather are used to distinguish one element from another. The terms “a” and “an” and “the” do not denote a limitation of quantity, and are to be construed to cover both the singular and the plural, unless otherwise indicated herein or clearly contradicted by context. “Or” means “and/or” unless clearly stated otherwise. Reference throughout the specification to “an aspect” means that a particular element described in connection with the aspect is included in at least one aspect described herein, and may or may not be present in other aspects. The term “combination thereof” as used herein includes one or more of the listed elements, and is open, allowing the presence of one or more like elements not named. In addition, it is to be understood that the described elements may be combined in any suitable manner in the various aspects. [0074] Unless specified to the contrary herein, all test standards are the most recent standard in effect as of the filing date of this application, or, if priority is claimed, the filing date of the earliest priority application in which the test standard appears. 22SHPP0074-WO-PCT (SS240080PCT) [0075] Unless defined otherwise, technical and scientific terms used herein have the same meaning as is commonly understood by one of skill in the art to which this application belongs. All cited patents, patent applications, and other references are incorporated herein by reference in their entirety. However, if a term in the present application contradicts or conflicts with a term in the incorporated reference, the term from the present application takes precedence over the conflicting term from the incorporated reference. [0076] Compounds are described using standard nomenclature. For example, any position not substituted by any indicated group is understood to have its valency filled by a bond as indicated, or a hydrogen atom. A dash ("-") that is not between two letters or symbols is used to indicate a point of attachment for a substituent. For example, -CHO is attached through carbon of the carbonyl group. [0077] As used herein, the term “hydrocarbyl”, whether used by itself, or as a prefix, suffix, or fragment of another term, refers to a residue that contains only carbon and hydrogen. The residue can be aliphatic or aromatic, straight-chain, cyclic, bicyclic, branched, saturated, or unsaturated. It can also contain combinations of aliphatic, aromatic, straight chain, cyclic, bicyclic, branched, saturated, and unsaturated hydrocarbon moieties. However, when the hydrocarbyl residue is described as substituted, it may, optionally, contain heteroatoms over and above the carbon and hydrogen members of the substituent residue. Thus, when specifically described as substituted, the hydrocarbyl residue can also contain one or more carbonyl groups, amino groups, hydroxyl groups, or the like, or it can contain heteroatoms within the backbone of the hydrocarbyl residue. The term "alkyl" means a branched or straight chain, saturated aliphatic hydrocarbon group, e.g., methyl, ethyl, n-propyl, i-propyl, n-butyl, s-butyl, t-butyl, n- pentyl, s-pentyl, and n- and s-hexyl. “Alkenyl” means a straight or branched chain, monovalent hydrocarbon group having at least one carbon-carbon double bond (e.g., ethenyl (-HC=CH2)). “Alkoxy” means an alkyl group that is linked via an oxygen (i.e., alkyl-O-), for example methoxy, ethoxy, and sec-butyloxy groups. "Alkylene" means a straight or branched chain, saturated, divalent aliphatic hydrocarbon group (e.g., methylene (-CH2-) or, propylene (-(CH2)3- )). “Cycloalkylene” means a divalent cyclic alkylene group, -C_nH_2n-x, wherein x is the number of hydrogens replaced by cyclization(s). “Cycloalkenyl” means a monovalent group having one or more rings and one or more carbon-carbon double bonds in the ring, wherein all ring members are carbon (e.g., cyclopentyl and cyclohexyl). "Aryl" means an aromatic hydrocarbon group containing the specified number of carbon atoms, such as phenyl, tropone, indanyl, or naphthyl. “Arylene” means a divalent aryl group. “Alkylarylene” means an arylene group substituted with an alkyl group. “Arylalkylene” means an alkylene group substituted with an 22SHPP0074-WO-PCT (SS240080PCT) aryl group (e.g., benzyl). The prefix "halo" means a group or compound including one more of a fluoro, chloro, bromo, or iodo substituent. A combination of different halo atoms (e.g., bromo and fluoro), or only chloro atoms can be present. The prefix “hetero” means that the compound or group includes at least one ring member that is a heteroatom (e.g., 1, 2, or 3 heteroatom(s)), wherein the heteroatom(s) is each independently N, O, S, Si, or P. “Substituted” means that the compound or group is substituted with at least one (e.g., 1, 2, 3, or 4) substituents that can each independently be a C1-9 alkoxy, a C1-9 haloalkoxy, a nitro (-NO2), a cyano (-CN), a C1-6 alkyl sulfonyl (-S(=O)2-alkyl), a C6-12 aryl sulfonyl (-S(=O)2-aryl), a thiol (-SH), a thiocyano (-SCN), a tosyl (CH₃C₆H₄SO₂-), a C_3-12 cycloalkyl, a C_2-12 alkenyl, a C_5-12 cycloalkenyl, a C_6-12 aryl, a C_{7- 13} arylalkylene, a C_4-12 heterocycloalkyl, and a C_3-12 heteroaryl instead of hydrogen, provided that the substituted atom’s normal valence is not exceeded. The number of carbon atoms indicated in a group is exclusive of any substituents. For example -CH₂CH₂CN is a C₂ alkyl group substituted with a nitrile. [0078] While particular embodiments have been described, alternatives, modifications, variations, improvements, and substantial equivalents that are or may be presently unforeseen may arise to applicants or others skilled in the art. Accordingly, the appended claims as filed and as they may be amended are intended to embrace all such alternatives, modifications variations, improvements, and substantial equivalents.

Claims

22SHPP0074-WO-PCT (SS240080PCT) CLAIMS 1. A polyetherimide comprising repeating units derived from a dianhydride selected from 4,4'-((propane-2,2-diylbis(4,1-phenylene))bis(oxy))bis(isobenzofuran-1,3-dione); or 4,4'-([1,1'-biphenyl]-4,4'-diylbis(oxy))bis(isobenzofuran-1,3-dione); a first diamine comprising 9,9-bis(4-aminophenyl)fluorene; and a second diamine comprising diaminodiphenyl ether, 4,4’-diaminodiphenyl sulfone, meta-phenylene diamine, or para-phenylene diamine. 2. The polyetherimide of claim 1, wherein the dianhydride is 4,4'-((propane-2,2-diylbis(4,1- phenylene))bis(oxy))bis(isobenzofuran-1,3-dione). 3. The polyetherimide of claim 1 or 2, wherein the dianhydride is 4,4'-([1,1'-biphenyl]-4,4'- diylbis(oxy))bis(isobenzofuran-1,3-dione). 4. The polyetherimide of claim 2 or 3, wherein the first diamine is 9,9-bis(4- aminophenyl)fluorene and the second diamine is 4,4’-diaminodiphenyl ether. 5. The polyetherimide of claim 2 or 3, wherein the first diamine is 9,9-bis(4- aminophenyl)fluorene and the second diamine is 4,4’-diaminodiphenyl sulfone 6. The polyetherimide of any of claims 1 to 5, wherein the first diamine is present in an amount of 60 mole percent to 98 mole percent, preferably 75 mole percent to 85 mole percent, and the second diamine is present in an amount of 2 mole percent to 40 mole percent, preferably 15 mole percent to 25 mole percent, each based on the total moles of the first diamine and the second diamine. 7. The polyetherimide of any of claims 1 to 6, wherein the polyetherimide has a weight average molecular weight of 30,000 g/mol to 65,000 g/mol, preferably 35,000 g/mol to 45,000 g/mol, as determined by gel permeation chromatography in dichloromethane relative to polystyrene standards. 22SHPP0074-WO-PCT (SS240080PCT) 8. The polyetherimide of any of claims 1 to 7, wherein the polyetherimide exhibits a glass transition temperature of greater than 275°C, as determined by differential scanning calorimetry. 9. The polyetherimide of any of claims 1 to 8, wherein the polyetherimide exhibits one or more of: a melt flow rate of greater than 7 g/10 min, as determined at 367 °C under a 6.7 kg load; or a transmission of at least 80% at 850 nm; or a yellowness index of less than 125, as determined according to ASTM D1925; or less than 5000 ppm, or less than 1000 ppm, or less than 100 ppm of elemental fluorine, as determined using combustion ion chromatography. 10. The polyetherimide of claim 1, wherein the dianhydride is 4,4'-((propane-2,2-diylbis(4,1- phenylene))bis(oxy))bis(isobenzofuran-1,3-dione), the first diamine is 9,9-bis(4-aminophenyl)fluorene, and the second diamine is diaminodiphenyl ether; wherein the polyetherimide has a weight average molecular weight of 35,000 g/mol to 45,000 g/mol; and wherein the polyetherimide exhibits: a viscosity of greater than 200 Pa-s, as determined according to ASTM D3835 at 400 °C and 5000 s^-1; and a melt flow rate of greater than 9 g/10 min, as determined at 367°C under a 6.7 kg load; and a transmission of at least 80% at 850 nm. 11. The polyetherimide of claim 10, wherein the polyetherimide exhibits a glass transition temperature of greater than 275 °C, preferably greater than 275 °C to 290 °C, as determined by differential scanning calorimetry. 12. A polymer composition comprising the polyetherimide of any of claims 1 to 11. 13. An article comprising the polyetherimide of any of claims 1 to 11 or the polymer composition of claim 12. 22SHPP0074-WO-PCT (SS240080PCT) 14. The article of claim 13, wherein the article is an optical article, preferably a lens or an optoelectronic component. 15. A method for the manufacture of the polyetherimide of any of claims 1 to 11, the method comprising: combining the dianhydride, the first diamine, and the second diamine under conditions effective to provide the polyetherimide.