IP Library › Granted Patent US 9,725,617
Granted Patent B2
US 9,725,617 · App. 14/687,771 · Granted Aug 8, 2017

Low toxicity solvent system for polyamideimide and polyamide amic acid resin coating

Inventors: Carissa M. Kelly (Dayton, TN); David E. Noga (Spring City, TN); John E. Sidenstick (Newport, TN); Limor Ben-Asher (Cresskill, NJ); Atsuo Kondo (Edgewater, NJ)
Assignee: FUJIFILM Hunt Chemicals U.S.A., Inc.
C09D179/08C08G18/345C08G18/7671C08G73/1035C08G73/1067C08G73/14C09D7/001
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Quick Facts
Patent No.
US 9,725,617
App. No.
14/687,771
Granted
Aug 8, 2017
Kind
B2
Abstract

A polyamideimide and polyamide amic acid resin polymer that allows for reduced levels of toxicity in manufacturing. In an embodiment, a coating composition comprises at least one polyamideimide resin, at least one aprotic dialkylamide solvent and at least one co-solvent. In another embodiment, the at least one co-solvent is selected from a 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.

Claims (23)

1. A coating composition comprising:

at least one polyamideimide resin;

at least one aprotic dialkylamide solvent selected from a group consisting of N-acetyl morpholine, diethyl acetamide, di-N-propyl acetamide, N-formyl morpholine, diacetylpiperazine, N,N-diisopropylacetamide, di-N-butylacetamide, di-N-propylacetamide and N-propionyl morpholine; and

at least one co-solvent is selected from a 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, ε-caprolactone and methylcyclohexane;

wherein a ratio of all aprotic dialkylamide solvents to all co-solvents is in a range from 95:5 to 55:4.

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

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

4. The coating composition of claim 1 , wherein the at least one co-solvent is selected from a 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 coating composition 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.

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

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

8. The coating composition of claim 1 , wherein the polyamideimide resin is a product of 4,4′-methylene diphenyldiisocyanate and trimellitic anhydride.

9. A coating composition comprising:

at least one polyamideimide resin;

at least one aprotic dialkylamide solvent selected from a group consisting of N-acetyl morpholine, diethyl acetamide, di-N-propyl acetamide, N-formyl morpholine, diacetylpiperazine, N,N-diisopropylacetamide, di-N-butylacetamide, di-N-propylacetamide and N-propionyl morpholine; and

at least one co-solvent is selected from a 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, 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-(di methylamino)-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, 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.

10. The coating composition of claim 9 , wherein the at least one aprotic dialkylamide solvent is N-acetyl morpholine.

11. The coating composition of claim 9 , wherein the at least one aprotic dialkylamide solvent is N-formyl morpholine.

12. The coating composition of claim 9 , wherein a ratio of all aprotic dialkylamide solvents to all co-solvents is in a range from 90:10 to 70:30.

13. The coating composition of claim 9 , wherein a ratio of the total of quantity of all aprotic dialkylamide solvents plus all co-solvents to polyamideimide is in a range from 85:15 to 60:40.

14. The coating composition of claim 9 , wherein a ratio of the total of quantity of all aprotic dialkylamide solvents plus all co-solvents to polyamideimide is in a range from 80:20 to 65:35.

15. The coating composition of claim 9 , wherein the polyamideimide resin is a product of 4,4′-methylene diphenyldiisocyanate and trimellitic anhydride.

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 May 23, 2016
From: KELLY, CARISSA M.; NOGA, DAVID E.; SIDENSTICK, JOHN E.; BEN-ASHER, LIMOR; KONDO, ATSUO
To: FUJIFILM HUNT CHEMICALS U.S.A., INC.
Reel/Frame 038690/0388 →
Continuity (2)
Provisional Application 61981155 · Apr 17, 2014
Related Publication 20150299513A1 · Oct 22, 2015