Process for polyimide synthesis and polyimides made therefrom

Patent metadata

Field	Value
Publication number	US-2023279182-A1
Application number	US-202018040291-A
Country	US
Kind code	A1
Filing date	Oct 5, 2020
Priority date	Aug 7, 2020
Publication date	Sep 7, 2023
Grant date	—

Abstract

The present disclosure describes methods of polyimide synthesis and polyimides made therefore. The method includes placing a tetracarboxylic compound and a solvent in a reaction vessel and adding a first amount of a diamine. The first amount of the diamine is not more than 99.5 mol % of the tetracarboxylic compound inside the reaction vessel. The method can include agitating the mixture and determining a viscosity of the mixture. The method can further include adding a second amount of the diamine. The last steps can be repeated until the viscosity increases to a target value. The target viscosity can be correlated to a peak weight-averaged molecular weight of the polyimide.

First claim

1 . A method for preparing a polyimide, the method comprising:
a) placing a tetracarboxylic compound and a solvent in a reaction vessel, b) adding a first amount of a diamine, wherein the first amount is not more than 99.5 mol %, not more than 99 mol %, not more than 98 mol %, not more than 97 mol %, not more than 96 mol %, or not more than 95 mol % of the tetracarboxylic compound to the reaction vessel to form a mixture, c) agitating the mixture, d) determining a viscosity of the mixture, e) adding a second amount of the diamine, f) repeating steps d) and e) until the viscosity increases to a target value.

2 . The method according to claim 1 , wherein the tetracarboxylic compound is selected from:

any tetracarboxylic acid thereof, or any combination thereof.

3 . The method according to claim 1 , wherein the diamine is selected from:

and any combination thereof.

4 . The method according to claim 1 , wherein the solvent is selected from ethylene glycol methyl ether, ethylene glycol butyl ether, 1-methoxy-2-propanol, 2-butoxyethanol, propylene glycol monomethyl ether, phenol, o-cresol, m-cresol, p-cresol, cresols, ethyl acetate, butyl acetate, ethylene glycol acetate, γ-butyrolactone, γ-valerolactone, propylene glycol acetate, ethyl lactate, acetone, methyl ethyl ketone, cyclopentanone, cyclohexanone, 2-heptanone, methyl isobutyl ketone, pentane, hexane, heptane, ethylcyclohexane, toluene, xylene, acetonitrile, tetrahydrofuran, dimethoxyethane, chloroform, chlorobenzene, N,N-dimethylacetamide, N,N-dimethylformamide, dimethyl sulfone, dimethyl sulfoxide, or any combination thereof.

5 . The method according to claim 1 , wherein step c) includes heating the mixture to a temperature of at least 40° C., at least 60° C., at least 80° C., at least 100° C., at least 110° C., at least 120° C., at least 130° C., at least 140° C., at least 150° C., or at least 160° C.

6 . The method according to claim 1 , wherein step b) includes adding a catalyst.

7 . The method according to claim 6 , wherein the catalyst is selected from N-ethylpiperidine, N-propylpiperidine, N-butylpyrrolidine, N-butylpiperidine, N-propylhexahydroazepine, azabicyclo[2.2.1]heptane, azabicyclo[3.2.1]octane, azabicyclo[2.2.2]octane, azabicyclo[3.2.2]nonane, 2-methylpyridine (2-picoline), 3-methylpyridine (3-picoline), 4-methylpyridine (4-Picoline), 2-ethylpyridine, 3-ethylpyridine, 4-ethylpyridine, 2,4-dimethylpyridine, 2,4,6-trimethylpyridine, 2,3-cyclopentenopyridine, 3,4-cyclopentenopyridine, 5,6,7,8-Tetrahydroisoquinoline, isoquinoline, or any combination thereof.

8 . The method according to claim 1 , wherein in step d) the viscosity is determined by a rotational viscometer, a vibrational viscometer, an oscillating viscometer, or by measuring torque of an impeller.

9 . The method according to claim 1 , wherein step f) includes correlating the viscosity to a weight-averaged molecular weight of a polyimide.

10 . The method according to claim 1 , further comprising
g) adding a precipitation agent to form a precipitate.

11 . The method according to claim 10 , wherein the precipitation agent is selected from water, methanol, ethanol, propanol, butanol, pentanol, acetic acid, ammonia, or any combination thereof.

12 . A polyimide formed by the method according to claim 1 .

13 . A polyimide material made from a diamine and a tetracarboxylic compound, wherein the diamine is selected from the group consisting of:

and any combination thereof;
wherein the polyimide material has at least one property selected from the following property group A and at least one property selected from the following property group B, wherein property group A comprises:
(i) a tensile strength as determined according to ASTM standard D897-08 of at least 2.4 GPa, at least 2.6 GPa, at least 2.8 GPa, at least 3.0 GPa, at least 3.2 GPa, at least 3.4 GPa, at least 3.6 GPa, at least 3.8 GPa, at least 4.0 GPa, at least 4.2 GPa, or at least 4.4 GPa;
(ii) a glass transition temperature as determined by thermomechanical analysis of at least 180° C., at least 185° C., at least 190° C., at least 195° C., at least 200° C., at least 205° C., at least 210° C., at least 215° C., at least 220° C., at least 225° C., at least 230° C., at least 235° C., at least 240° C., at least 245° C., at least 250° C., at least 255° C., at least 260° C., at least 265° C., at least 270° C., at least 275° C., at least 280° C., at least 285° C., at least 290° C., at least 295° C., at least 300° C., or at least 305° C.;
(iii) a peak molecular weight as determined by size exclusion chromatography against a polystyrene standard of at least 200 kDa, at least 250 kDa, at least 300 kDa, at least 350 kDa, at least 400 kDa, at least 450 kDa, at least 500 kDa, at least 550 kDa, at least 600 kDa, at least 650 kDa, or at least 700 kDa; or
(iv) an elongation at break of a 100 micron film of the polyimide film as determined by ASTM D638-14 of not more than 10%, not more than 9.5%, not more than 9%, not more than 8.5%, not more than 8%, not more than 7.5%, not more than 7%, not more than 6.5%, not more than 6.2%, not more than 6.0%, not more than 5.8%, not more than 5.6%, not more than 5.4%, not more than 5.2%, not more than 5%, or not more than 4.8%; and
property group B comprises:
(i) an optical transparency of a 100 micron film of the polyimide material as determined by UV-Vis spectroscopy at 400 nm of at least 80%, at least 82%, at least 84%, at least 86%, at least 88%, at least 90%, at least 92%, at least 94%, at least 96%, or at least 98%;
(ii) an optical transparency of a 100 micron film of the polyimide material as determined by UV-Vis spectroscopy at 550 nm of at least 85%, at least 86%, at least 87%, at least 88%, at least 89%, at least 90%, at least 91%, at least 92%, at least 94%, or at least 96%;
(iii) an optical transparency of a 100 micron film of the polyimide material as determined by UV-Vis spectroscopy at 300 nm of not greater than 50%, not greater than 48%, not greater than 46%, not greater than 44%, not greater than 42%, not greater than 40%, not greater than 38%, not greater than 36%, not greater than 34%, not greater than 32%, not greater than 30%, not greater than 28%, not greater than 26%, not greater than 24%, not greater than 22%, not greater than 20%, not greater than 18%, or not greater than 16%;
(iv) a thickness retardation R th of not more than 100 nm, not more than 80 nm, not more than 60 nm, not more than 50 nm, not more than 40 nm, not more than 30 nm, not more than 28 nm, not more than 26 nm, not more than 24 nm, not more than 22 nm, or not more than 20 nm; or
(v) a Yellow Index according to ASTM E313 of not more than 4.0, not more than 3.5, not more than 3.2, not more than 3.0, not more than 2.8, not more than 2.6, not more than 2.4, not more than 2.2, not more than 2.0, not more than 1.8, not more than 1.6, or not more than 1.4.

14 . The polyimide material according to claim 13 having at least two, at least three, or at least four properties of property group A.

15 . The polyimide material according to claim 13 having at least two, at least three, or at least four properties of property group B.

16 . The polyimide material according to

Assignees

• Zymergen Inc
• Sumitomo Chemical Co

Inventors

• Kerszulis Justin
• Kannan Abhiram
• Poliak Peter Lucas
• Lopez Liza
• Hull Kelby
• Homyak Patrick
• Chachra Gaurav
• Mcgann Christopher Leland
• Zoombelt Arjan
• Ishiwata Koji

Classifications

• C09D179/08

  Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors · CPC title

• C08G2150/00

  Compositions for coatings · CPC title

• C08G73/1028

  characterised by the process itself, e.g. steps, continuous · CPC title

• C08G73/1007 Primary

  from tetracarboxylic acids or derivatives and diamines · CPC title

• C08G73/1032

  characterised by the solvent(s) used · CPC title