IP Library › Granted Patent US 9,815,941
Granted Patent B2
US 9,815,941 · App. 14/687,776 · Granted Nov 14, 2017

Low toxicity solvent system for polyamdieimide and polyamide amic acid resin manufacture

Inventors: Carissa M. Kelly (Dayton, TN); David E. Noga (Spring City, TN); John E. Sidenstick (Newport, TN); Limor Ben-Asher (Cresskill, NJ); Atuso Kondo (Edgewater, NJ)
Assignee: CYMER-DAYTON, LLC
C08G73/14C08G73/1003C08G73/1035C09D179/08
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Quick Facts
Patent No.
US 9,815,941
App. No.
14/687,776
Granted
Nov 14, 2017
Kind
B2
Abstract

Techniques and mechanisms to reduce toxicity in manufacturing of a polyamideimide and polyamide amic acid resin polymer. In an embodiment, a polyamideimide is produced using at least one aprotic dialkylamide solvent and at least one co-solvent. In another embodiment, the at least one co-solvent is selected from the group consisting of methyl actetate, n-propyl acetate, t-butyl acetate, iso-butyl acetate, ethyl acetate, isopropyl acetate, methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, n-butyl lactate, isobutyl lactate, t-butyl lactate, cyclohexanone, cyclopentanone, n-butyl acetate, methyl alcohol, ethyl alcohol, isopropyl alcohol, n-acetyl morpholine, ε-caprolactone and methylcyclohexane.

Claims (15)

1. A process for producing polyamideimide, the process consisting of:

using at least one aprotic dialkylamide solvent and at least one co-solvent during synthesis of polyamideimide, wherein the at least one aprotic dialkylamide solvent is N-acetyl morpholine or N-formyl morpholine.

2. The process of claim 1 , wherein the at least one aprotic dialkylamide solvent is N-acetyl morpholine.

3. The process of claim 1 , wherein the at least one aprotic dialkylamide solvent is N-formyl morpholine.

4. The process of claim 1 , wherein the at least one co-solvent is selected from the group consisting of methyl acetate, n-propyl acetate, ethyl acetate, isopropyl acetate, ethyl lactate, n-propyl lactate, n-butyl lactate, cyclohexanone, cyclopentanone, n-butyl acetate, isopropyl alcohol, ε-caprolactone and methylcyclohexane.

5. The process of claim 1 , wherein the at least one co-solvent is selected from the group consisting of methyl acetate, n-propyl acetate, ethyl acetate, isopropyl acetate, ethyl lactate, n-propyl lactate, n-butyl lactate, cyclohexanone, n-butyl acetate, isopropyl alcohol, ε-caprolactone and methylcyclohexane.

6. The process of claim 1 , wherein a ratio of all aprotic dialkylamide solvents to all co-solvents is in a range from 90:10 to 70:30.

7. The process of claim 1 , wherein a ratio of the total of all aprotic dialkylamide solvents plus all co-solvents to polyamideimide is in a range from 85:15 to 60:40.

8. The process of claim 1 , wherein a ratio of the total of all aprotic dialkylamide solvents plus all co-solvents to polyamideimide is in a range from 80:20 to 65:35.

9. The process of claim 1 , wherein the polyamideimide is the product of 4,4′-methylene diphenyldiisocyanate and trimellitic anhydride.

10. A polyamideimide composition product of the process of claim 1 .

11. A process for producing polyamideimide, the process consisting of:

using at least one aprotic dialkylamide solvent and at least one co-solvent during synthesis of polyamideimide, wherein the at least one co-solvent is selected from the group consisting of methyl acetate, n-propyl acetate, t-butyl acetate, iso-butyl acetate, ethyl acetate, isopropyl acetate, methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, n-butyl lactate, isobutyl lactate, t-butyl lactate, cyclohexanone, cyclopentanone, n-butyl acetate, methyl alcohol, ethyl alcohol, isopropyl alcohol, n-acetyl morpholine, ε-caprolactone and methylcyclohexane, wherein a ratio of all aprotic dialkylamide solvents to all co-solvents is in a range from 95:5 to 55:45.

12. A process for producing polyamideimide, the process consisting of:

using at least one aprotic dialkylamide solvent and at least one co-solvent during synthesis of polyamideimide, wherein the at least one co-solvent is selected from the group consisting of methyl acetate, n-propyl acetate, t-butyl acetate, iso-butyl acetate, ethyl acetate, isopropyl acetate, methyl lactate, ethyl lactate, n-propyl lactate, isopropyl lactate, n-butyl lactate, isobutyl lactate, t-butyl lactate, cyclohexanone, cyclopentanone, n-butyl acetate, methyl alcohol, ethyl alcohol, isopropyl alcohol, anisol, n-acetyl morpholine, ε-caprolactone, methylcyclohexane, N-n-butylpyrrolidone, N-isobutylpyrrolidone, N-t-butylpyrrolidone, N-n-pentylpyrrolidone, N-(methyl-substituted butyl)pyrrolidone, ring-methyl-substituted N-propyl pyrrolidone, ring-methyl-substituted N-butyl pyrrolidone, N-(methoxypropyl)pyrrolidone, N-(methoxypropyl)pyrrolidone, 1,5-dimethyl-pyrrolidone and isomers thereof, dipropylene glycol dimethyl ether, a mixture including ethyl lactate and an ethyl ester derived from soya bean oil or corn oil, poly(ethylene glycol)dimethyl ether, diethylene glycol diethyl ether, 1,3-dioxolane, dimethyl sulphoxide, methyl-5-(dimethylamino)-2-methyl-5-oxopentanoate, TamiSolve®NxG, propylene glycol methyl ether acetate, choline hydroxide, propylene carbonate, diethyl carbonate, glycerine carbonate, dimethylisopropylamine and isomers thereof, dihydrolevo glucosenone, octyl pyrrolidone and isomers thereof, N-methyl-ε-caprolactam, N,N,N′,N′-tetramethylguanidine, 2-pyrrolidone, 2,2-dimethyl dioxolane-4-methanol and isomers thereof, Rhodiasolv® RPDE-K, Rhodiasolv® PolarClean, Rhodiasolv® Infinity, Rhodiasolv® IRIS, diethylethanolamine, N-ethylmorpholine, γ-hexalactone, tetrahydrofuran, furfuryl alcohol, acetophenone, cumene, cyclopentylmethyl ether, methyl-tetrahydrofuran, N-octyl pyrrolidone, dioxalane, methylethylketone, dimethylsuccinate, N-methylcaprolactame and N-cyclohexylpyrrolidone, wherein a ratio of all aprotic dialkylamide solvents to all co-solvents is in a range from 95:5 to 55:45.

Assignments (2)
ASSET PURCHASE AGREEMENT Recorded Sep 20, 2017
From: FUJIFILM HUNT CHEMICALS USA, INC.
To: CYMER-DAYTON, LLC
Reel/Frame 043924/0026 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Jun 8, 2016
From: KONDO, ATSUO; KELLY, CARISSA M.; NOGA, DAVID E.; SIDENSTICK, JOHN; BEN-ASHER, LIMOR
To: FUJIFILM HUNT CHEMICALS U.S.A., INC.
Reel/Frame 038845/0904 →
Continuity (2)
Provisional Application 61981157 · Apr 17, 2014
Related Publication 20150299393A1 · Oct 22, 2015