WO2023211747A1 - Polyamide-imide optiquement transparent - Google Patents

Polyamide-imide optiquement transparent Download PDF

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Publication number
WO2023211747A1
WO2023211747A1 PCT/US2023/019198 US2023019198W WO2023211747A1 WO 2023211747 A1 WO2023211747 A1 WO 2023211747A1 US 2023019198 W US2023019198 W US 2023019198W WO 2023211747 A1 WO2023211747 A1 WO 2023211747A1
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WIPO (PCT)
Prior art keywords
gpa
polyamideimide
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accordance
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PCT/US2023/019198
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English (en)
Inventor
Patrick HOMYAK
Arjan Zoombelt
Michael William Angus Maclean
Kazuya Matsui
Satoshi Okamoto
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Zymergen Inc.
Sumitomo Chemical Company, Limited
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Application filed by Zymergen Inc., Sumitomo Chemical Company, Limited filed Critical Zymergen Inc.
Publication of WO2023211747A1 publication Critical patent/WO2023211747A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/14—Polyamide-imides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1039—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors comprising halogen-containing substituents
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/10—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
    • C08G73/1075—Partially aromatic polyimides
    • C08G73/1082—Partially aromatic polyimides wholly aromatic in the tetracarboxylic moiety
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
    • C08J5/18—Manufacture of films or sheets
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2379/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen with or without oxygen, or carbon only, not provided for in groups C08J2361/00 - C08J2377/00
    • C08J2379/04—Polycondensates having nitrogen-containing heterocyclic rings in the main chain; Polyhydrazides; Polyamide acids or similar polyimide precursors
    • C08J2379/08—Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors

Definitions

  • the present disclosure relates to optically transparent polyamideimides.
  • Organic films are high in flexibility as compared to glass, difficult to break, and lightweight. Recently, a study has been performed with the aim of developing a flexible display using organic film as the substrate of a flat panel display.
  • resins used in organic film include polyester, polyamide, polyimide, polyamideimide, polycarbonate, polyether sulfone, acrylic, and epoxy.
  • polyamideimide resin is high in heat resistance, mechanical strength, abrasion resistance, dimensional stability, chemical resistance, insulation capability, and accordingly in wide use in the electric/electronic industries.
  • polyamideimide resin For use as an alternative to the glass substrate in display elements, polyamideimide resin should also have high transparency and low birefringence. These properties are necessary to obtain clear images.
  • manufacturing methods provide inconsistencies in resins leading to variation in performance properties. Accordingly, there is a need for devising and improving processes that lead to performance consistency.
  • a polyamideimide includes a moiety selected from:
  • an optical stack includes a polyamideimide according to the foregoing first aspect.
  • an electronic device includes a polyamideimide according to the foregoing first aspect.
  • a polyamideimide film includes a moiety selected from:
  • a method of forming a polyamideimide includes: polymerizing at least one dianhydride monomer and at least one diamine monomer to form the polyamideimide, wherein the polyamideimide includes at least one moiety selected from:
  • any suitable derivative means any chemical compound capable of producing the same chemical reaction product as the compounds listed in the sentences with the term “any suitable derivative.”
  • any suitable derivatives are chemical compounds that yield the same polyamide-imide, such as the acid bromide, or an ester derivative of compound A.
  • the term “about” means +/- 10% of any recited value. As used herein, this term modifies any recited value, range of values, or endpoints of one or more ranges.
  • top As used herein, the terms “top,” “bottom,” “upper,” “lower,” “above,” and “below” are used to provide a relative relationship between structures. The use of these terms does not indicate or require that a particular structure must be located at a particular location in the apparatus.
  • the terms “comprises”, “comprising”, “includes”, “including”, “has”, “having” or any other variation thereof, are open-ended terms and should be interpreted to mean “including, but not limited to. . . .” These terms encompass the more restrictive terms “consisting essentially of’ and “consisting of.”
  • a method, article, or apparatus that comprises a list of features is not necessarily limited only to those features but may include other features not expressly listed or inherent to such method, article, or apparatus.
  • “or” refers to an inclusive-or and not to an exclusive-or. For example, a condition A or B is satisfied by any one of the following: A is true (or present), and B is false (or not present), A is false (or not present), and B is true (or present), and both A and B are true (or present).
  • ratios, concentrations, amounts, and other numerical data may be expressed herein in a range format. It is to be understood that such a range format is used for convenience and brevity, and thus, should be interpreted in a flexible manner to include not only the numerical values explicitly recited as the limits of the range, but also to include all the individual numerical values or sub-ranges encompassed within that range as if each numerical value and sub-range is explicitly recited. To illustrate, a concentration range of “about 0.1% to about 5%” should be interpreted to include not only the explicitly recited concentration of about 0.1 wt. % to about 5 wt.
  • the term “about” can include traditional rounding according to significant figures of the numerical value.
  • the phrase “about ‘x’ to ‘y’” includes “about ‘x’ to about ‘y’”.
  • a polyamideimide includes a moiety selected from:
  • the polyamideimide is selected from the moiety consisting essentially of: combination thereof. In another embodiment, the polyamideimide is selected from the moiety consisting of: combination thereof. In one embodiment, the polyamideimide is formed into a film.
  • the film has advantageous properties such as structural, thermal, mechanical, and optical properties. For instance, the film has at least two properties including, but not limited to:
  • a pencil hardness of greater than HB greater than 1H, greater than 2H, greater than 3H, greater than 4H, greater than 5H, or greater than 6H;
  • a coefficient of moisture expansion as determined according to ASTM D5229/D5229M-14 of not greater than 50 ppm, not greater than 45 ppm, not greater than 40 ppm, not greater than 35 ppm, not greater than 30 ppm, not greater than 25 ppm, not greater than 20 ppm, or not greater than 15 ppm;
  • the polyamideimide film has at least two, at least three, or at least four properties selected from (i) through (ix).
  • the polyamideimide film has at least three properties selected from (i) through (ix), at least four properties selected from (i) through (ix), at least five properties selected from (i) through (ix), at least six properties selected from (i) through (ix), at least seven properties selected from (i) through (ix), at least eight properties selected from (i) through (ix), or all properties selected from (i) through (ix).
  • the polyamideimide is formed with at least one moiety including a diamine reacted with at least one moiety including a dianhydride. Any reasonable diamine is envisioned. In an embodiment, the diamine is selected from: combination thereof.
  • the diamine consists essentially of: diamine of formula (13) is also known as Nl,N4-bis[4-(2-aminoethyl)phenyl]benzene-l,4- dicarboxamide (APEA TPC 1).
  • the diamine of formula (14) is also known as Nl,N4-bis[2-aminoethyl)phenyl]benzene-l,4- dicarboxamide (APEA TPC 1).
  • the diamine of formula (14) is also known as Nl,N4-bis[2-
  • the diamine can be selected independently for each occasion from the group consisting of: combination thereof.
  • the polyamideimide is further formed with at least one moiety including at least one dianhydride. Any dianhydride is envisioned. In a particular embodiment, the dianhydride is selected from:
  • the dianhydride is selected from the group consisting essentially of: , also known as “6FDA”.
  • the dianhydride is selected from the group consisting of:
  • the diamine moiety and the dianhydride moiety can be in any molar ratio.
  • the molar ratio of the diamine moiety : dianhydride moiety can range from 10:1 to 1:10, from 5:1 to 1:5, from 3:1 to 1:3, from 2:1 to 1:2, from 3:2 to 2:3, from 4:3 to 3:4, from 5:4 to 4:5, from 6:5 to 5:6, from 7:6 to 6:7, from 8:7 to 7:8, from 9:8 to 8:9, or from 10:9 to 9:10.
  • the diamine moiety is in the majority.
  • the polyamideimide may include a third, a fourth, and further moieties.
  • the molar ratio of first to the sum of all other monomers can range from 10:1 to 1: 10, from 5:1 to 1:5, from 3:1 to 1:3, from 2:1 to 1:2, from 3:2 to 2:3, from 4:3 to 3:4, from 5:4 to 4:5, from 6:5 to 5:6, from 7:6 to 6:7, from 8:7 to 7:8, from 9:8 to 8:9, or from 10:9 to 9:10.
  • an optical stack can include a polyamideimide according to the first aspect or its embodiments.
  • the polyamideimide can form a rear or backing layer or a cover layer of the optical stack.
  • the polyamideimide can be a substrate to the nanocircuitry of an optical stack.
  • the polyamideimide can form the horizontal or vertical polarizer of an optical stack or the layers adjacent to the liquid crystal layers.
  • the optical stack is an LED or an OLED assembly.
  • the polyamideimide layer can be a substrate or cover layer of the LED or OLED assembly.
  • an electronic device includes a polyamideimide according to the first aspect.
  • the electronic device can include but is not limited to telephones, cell phones, personal computers, desktop computers, laptops, tablet computers, printers, flatscreen TVs, music players, digital cameras, camcorders, video game consoles, remote controls, smart appliances, automobile control displays, marine and aviation transport control systems.
  • a method of forming a polyamideimide includes polymerizing at least one dianhydride monomer and at least one diamine monomer to form the polyamideimide.
  • the polyamideimide formed includes at least one moiety selected from polyamideimide moiety described above.
  • the at least one dianhydride monomer and at least one diamine monomer can be selected from the dianhydride monomer and diamine monomer described above.
  • Embodiment 1 A polyamideimide including a moiety selected from:
  • Embodiment 2 The polyamideimide in accordance with embodiment 1, wherein the polyamideimide is a film, the film including at least two properties selected from:
  • a pencil hardness of greater than HB greater than 1H, greater than 2H, greater than 3H, greater than 4H, greater than 5H, or greater than 6H;
  • a coefficient of moisture expansion as determined according to ASTM D5229/D5229M-14 of not greater than 50 ppm, not greater than 45 ppm, not greater than 40 ppm, not greater than 35 ppm, not greater than 30 ppm, not greater than 25 ppm, not greater than 20 ppm, or not greater than 15 ppm;
  • Embodiment 3 The polyamideimide in accordance with embodiment 2, including at least three properties selected from (i) through (ix), at least four properties selected from (i) through (ix), at least five properties selected from (i) through (ix), at least six properties selected from (i) through (ix), at least seven properties selected from (i) through (ix), at least eight properties selected from (i) through (ix), or all properties selected from (i) through (ix).
  • Embodiment 4 The polyamideimide in accordance with any of the preceding embodiments, formed with at least one moiety including at least one diamine.
  • Embodiment 5 The polyamideimide in accordance with embodiment 4, wherein the diamine is selected from the group consisting of:
  • Embodiment 6 The polyamideimide in accordance with any of the preceding embodiments, formed with at least one moiety including at least one dianhydride.
  • Embodiment 7 The polyamideimide in accordance with embodiment 6, wherein the dianhydride is selected from the group consisting of:
  • Embodiment 8 The polyamideimide in accordance with embodiment 7, wherein the dianhydride is selected from:
  • Embodiment 9 The polyamideimide in accordance with embodiments 4-8, wherein the diamine and the dianhydride are in a molar ratio ranging from 10:1 to 1:10, from 5:1 to 1:5, from 3:1 to 1:3, from 2:1 to 1:2, from 3:2 to 2:3, from 4:3 to 3:4, from 5:4 to 4:5, from
  • Embodiment 10 An optical stack including the polyamideimide according to embodiments 1 through 9.
  • Embodiment 11 An electronic device including the polyamideimide according to embodiments 1 through 9.
  • Embodiment 12 A polyamideimide film including a moiety selected from: combination thereof.
  • Embodiment 13 The polyamideimide film in accordance with embodiment 12, wherein the polyamideimide film includes at least two properties selected from:
  • a pencil hardness of greater than HB greater than 1H, greater than 2H, greater than 3H, greater than 4H, greater than 5H, or greater than 6H;
  • a coefficient of moisture expansion as determined according to ASTM D5229/D5229M-14 of not greater than 50 ppm, not greater than 45 ppm, not greater than 40 ppm, not greater than 35 ppm, not greater than 30 ppm, not greater than 25 ppm, not greater than 20 ppm, or not greater than 15 ppm;
  • Embodiment 14 The polyamideimide film in accordance with embodiment 13, including at least three properties selected from (i) through (ix), at least four properties selected from (i) through (ix), at least five properties selected from (i) through (ix), at least six properties selected from (i) through (ix), at least seven properties selected from (i) through (ix), at least eight properties selected from (i) through (ix), or all properties selected from (i) through (ix).
  • Embodiment 15 The polyamideimide film in accordance with embodiments 12-14, formed with at least one moiety including at least one diamine selected from the group combination thereof.
  • Embodiment 16 The polyamideimide film in accordance with embodiments 12-15, formed with at least one dianhydride.
  • Embodiment 17 The polyamideimide film in accordance with embodiment 16, wherein the dianhydride is selected from the group consisting of:
  • Embodiment 18 The polyamideimide film in accordance with embodiment 17, wherein the dianhydride is selected from:
  • Embodiment 19 The polyamideimide film in accordance with embodiment 18, wherein the diamine and the dianhydride are in a molar ratio ranging from 10:1 to 1:10, from 5:1 to 1:5, from 3:1 to 1:3, from 2:1 to 1:2, from 3:2 to 2:3, from 4:3 to 3:4, from 5:4 to 4:5, from 6:5 to 5:6, from 7:6 to 6:7, from 8:7 to 7:8, from 9:8 to 8:9, or from 10:9 to 9:10.
  • Embodiment 20 The polyamideimide film in accordance with embodiments 12-19, wherein the moiety consists essentially of: combination thereof.
  • Embodiment 21 The polyamideimide film in accordance with embodiment 20, wherein the moiety consists of: combination thereof.
  • Embodiment 22 A method of forming a polyamideimide including: polymerizing at least one dianhydride monomer and at least one diamine monomer to form the polyamideimide, wherein the polyamideimide comprises at least one moiety selected from:
  • Embodiment 23 The method in accordance with embodiment 22, wherein the diamine is selected from the group consisting of: bination thereof.
  • Embodiment 24 The method in accordance with embodiment 22, wherein the dianhydride is selected from the group consisting of:
  • Embodiment 25 The method in accordance with embodiments 22-24, wherein the diamine and the dianhydride are in a molar ratio ranging from 10:1 to 1:10, from 5:1 to 1:5, from 3:1 to 1:3, from 2:1 to 1:2, from 3:2 to 2:3, from 4:3 to 3:4, from 5:4 to 4:5, from 6:5 to 5:6, from 7:6 to 6:7, from 8:7 to 7:8, from 9:8 to 8:9, or from 10:9 to 9:10.
  • Embodiment 26 The method in accordance with embodiments 22-25, wherein the polyamideimide is formed into a film.
  • Embodiment 27 The method in accordance with embodiment 26, wherein the film has a tensile modulus according to ASTM D638-14of at least 3 GPa, at least 5.2 GPa, at least 5.4 GPa, at least 5.6 GPa, at least 5.8 GPa, at least 6 GPa, at least 6.2 GPa, at least 6.4 GPa, at least 6.6 GPa, at least 6.8 GPa, at least 7 GPa, at least 7.2 GPa, at least 7.4 GPa, at least 7.6 GPa, at least 7.8 GPa, at least 8 GPa, at least 8.2 GPa, at least 8.5 GPa, at least 9 GPa, or at least 10 GPa.
  • ASTM D638-14of at least 3 GPa, at least 5.2 GPa, at least 5.4 GPa, at least 5.6 GPa, at least 5.8 GPa, at least 6 GPa, at least 6.2 GPa, at
  • Nl,N4-bis[4-(2-aminoethyl)phenyl]benzene-l,4-dicarboxamide (APEA TPC 1) was added as a solid and rinsed in with solvent (10.809g, 26.856mmole, 1 eq).
  • Polyamide-imide material can be dissolved in a solvent at a concentration ranging from 10 to 20 weight percent to form a varnish.
  • Solvents can be N,N- dimethylacetamide (DMAc), Cyclopentanone (CPN), Cyclohexanone (CHN), y- Butyrolactone (GBL), or Acetophenone (PhAc).
  • DMAc N,N- dimethylacetamide
  • CCN Cyclopentanone
  • CHN Cyclohexanone
  • GBL y- Butyrolactone
  • Acetophenone PhAc
  • the varnish can be coated on a flat surface such as a glass plate or a flexible carrier substrate and subsequently be dried. After the initial drying step, the film can be delaminated from the flat surface and further processed.
  • PAI films of the powders from Experiment 1 were prepared by first dissolving a portion of the powder in solvent (DMAc) at an approximate concentration of 10-20wt% to produce a colorless viscous varnish. The varnish was then coated onto a glass substrate via a doctor blade and heated at a temperature of 80°C for 30 minutes to produce a ‘wet’ PAI film.
  • solvent DMAc
  • the film was then removed from the plate and mounted into a stainless steel frame and baked under vacuum at 250°C for 12 hours, producing a dry, final colorless PAI film.
  • Film thickness The thickness of a polyamide-imide film was measured using a Mahr, 2057551 Marameter XLI-57B-15 Portable Thickness Gage. Typically, 6 to 21 measurements were taken across the film and the average value was reported.
  • the optical properties (e.g., percent transmittance, color, haze, R*) of a polyamide-imide film were measured using spectrophotometry.
  • the percent transmittance of the polyamide-imide film was measured using a Shimadzu UV-2700 equipped with an integrating sphere (ISR-2600).
  • ISR-2600 an integrating sphere
  • films were inserted into a film sample holder and transmittance was measured from 800 nm to 200 nm using a slit width of 5 nm with the transmittance at 380nm and 400nm (T38o% and T4oo%) reported. Maximum transmission was also measured at 550nm (T max ).
  • the color and haze of a polyamide-imide film was measured using an X-rite Ci7800 spectrophotometer. Typically, a film sample was placed in a 25 mm sample holder and a Class I continuous wave 532 nm laser was flashed through the sample to measure direct and total transmittance as well as haze. The average of three measurements was reported. Yellow index (YI) was measured according to ASTM E313-20. Haze was determined according to ASTM D1OO3-13.
  • the R* of a polyamide-imide film was measured using an Axometrics AxoScanTM Mueller Matrix Polarimeter. Typically, the film R* is measured by taking two axis out-of-plane retardance measurements at 550 nm wavelength in increments of 10° up to a maximum tilt angle of 50°; several spots are measured per film and the lowest R* value is reported.
  • Thermal properties - Incomplete imidization, residual solvent and thermal stability Ta were assessed using thermogravimetric analysis utilizing a TA Instruments Discovery TGA550. Typically, a few milligrams of polymer film were placed in a TGA pan which was heated at a rate of 10°C/min to 550°C under a nitrogen purge of 40-60 mL/min. The temperature at which 1% mass loss was achieved is recorded as the Ta (1%); for dry films (i.e., fully imidized, no residual solvent) this would typically occur in the 375-450°C temperature range for these materials.
  • the glass transition (T g ) of a polyamide-imide film was measured using dynamic mechanical analysis utilizing a TA Instruments Discovery DMA850 equipped with a film/fiber accessory. Typically, a 5 x 30 mm sample was die punched and loaded into the film/fiber accessory clamp; the film was heated at 5°C/min rate to 350-400°C in a nitrogen purged atmosphere under a 0.1% strain oscillated at 1Hz. The glass transition measurement was determined from the onset of the drop in storage modulus and/or the tan 6 maximum. The glass transition and coefficient of thermal expansion (CTE) of a polyamide-imide film was measured using thermal mechanical analysis utilizing a TA Instruments TMA Q400 with a film/fiber accessory.
  • CTE coefficient of thermal expansion
  • a 5 x 30 mm sample was used for testing.
  • the sample was heated at 3 °C/min to 350-400 °C under a nitrogen purge of 50 mL/min with a load of 0.5 g per film thickness in um.
  • CTE can be calculated using the slope of the line between 100-200°C.
  • the T g was calculated by measuring the temperature at which elongation of the sample occurs.
  • the specimens were tested following ASTM 1708.
  • the sample dimensions follow those listed in ASTM 1708 and thickness was measured for each film utilizing a Mahr GmbH 1086Ri 25/0, 0005mm (1’7.00002”). Measured force and sample displacement were used by the Instron to calculate the modulus, tensile strength, and elongation at break. Elongation at break was tested following ASTM D638-14 and tensile modulus via ASTM D638-14.

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
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  • Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)

Abstract

Un polyamide-imide comprend au moins une fraction ayant une structure de diamine étendue. Le polyamide-imide présente des propriétés optiques, structurales, thermiques, mécaniques souhaitables, ou une combinaison de celles-ci.
PCT/US2023/019198 2022-04-29 2023-04-20 Polyamide-imide optiquement transparent WO2023211747A1 (fr)

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5124428A (en) * 1991-05-31 1992-06-23 Amoco Corporation Amide-imide resin for production of heat-resistant fiber
US6028159A (en) * 1997-12-31 2000-02-22 Samsung Electronics Co., Ltd. Polyamideimide for optical communications and method for preparing the same
US20190077915A1 (en) * 2016-06-01 2019-03-14 Lg Chem, Ltd. High-strength transparent polyamidimide and method for preparing same
JP2020019938A (ja) * 2018-07-19 2020-02-06 住友化学株式会社 ポリアミドイミド樹脂
WO2022187797A1 (fr) * 2021-03-05 2022-09-09 Zymergen Inc. Polyamide-imides optiquement transparents

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5124428A (en) * 1991-05-31 1992-06-23 Amoco Corporation Amide-imide resin for production of heat-resistant fiber
US6028159A (en) * 1997-12-31 2000-02-22 Samsung Electronics Co., Ltd. Polyamideimide for optical communications and method for preparing the same
US20190077915A1 (en) * 2016-06-01 2019-03-14 Lg Chem, Ltd. High-strength transparent polyamidimide and method for preparing same
JP2020019938A (ja) * 2018-07-19 2020-02-06 住友化学株式会社 ポリアミドイミド樹脂
WO2022187797A1 (fr) * 2021-03-05 2022-09-09 Zymergen Inc. Polyamide-imides optiquement transparents

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
MASATOSHI HASEGAWA: "Development of Solution-Processable, Optically Transparent Polyimides with Ultra-Low Linear Coefficients of Thermal Expansion", POLYMERS, vol. 9, no. 12, pages 520, XP055549597, DOI: 10.3390/polym9100520 *

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