# US 9,751,986 B2 · Low toxicity solvent system for polyamideimide resins and solvent system manufacture

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- Number: US 9,751,986 B2
- Document ID: US9751986B2
- Status: Granted
- Kind: B2
- Application number: 14/365,459
- Filed: 2012-12-17
- Published: 2016-01-07
- Granted: 2017-09-05
- Earliest claimed: 2011-12-15
- Assignees: Fujifilm Hunt Chemicals US, Inc.
- Applicants: FUJIFILM Hunt Chemicals U.S.A., Inc.
- Inventors: John Sidenstick; David Noga; Kathryn Mullins; Mace Phillips
- Web page: https://patentgrep.com/patent/US9751986B2

## CPC

- C08G 73/14: Polyamide-imides
- C08G 73/1003: {Preparatory processes}
- C09D 7/20: Diluents or solvents
- C09D 179/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08L 79/08: Polyimides; Polyester-imides; Polyamide-imides; Polyamide acids or similar polyimide precursors
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C08L: COMPOSITIONS OF MACROMOLECULAR COMPOUNDS (compositions based on polymerisable monomers C08F, C08G; artificial filaments or fibres D01F; textile treating compositions D06)

## Abstract

Disclosed is a low toxicity aprotic alkyl amide solvent system used for the manufacture and application of polyamideimide resins, and an efficient method for manufacturing the polyamideimide resins in a solvent system in a single reaction with distillation which allows recycling of intermediate streams. The solvent system can be used for either the manufacture or the dissolution of polyamideimide resins.

## Claims

### Claim 1

A process for producing polyamideimide comprising using at least one aprotic dialkylamide solvent, wherein the at least one aprotic dialkylamide solvent includes diacetylpiperazine or N,N-diisopropylacetamide;
wherein a ratio of the at least one aprotic dialkylamide solvent to other process co-solvents is between 19:1 and 1:1; and
wherein the other process co-solvents are selected from the group consisting of water, o-xylene, triethylamine, dimethylethanolamine, morpholine, N-methylmorpholine, acetone, trimethylamine, tripropylamine, diethylamine, diisopropylamine, and caprolactam.

### Claim 2 (depends on 1)

The process of claim 1 wherein the at least one aprotic dialkylamide solvent further comprises N-acetyl morpholine.

### Claim 3 (depends on 1)

The process of claim 1 wherein the at least one aprotic dialkylamide solvent further comprises diethyl acetamide.

### Claim 4 (depends on 1)

The process of claim 1 wherein the at least one aprotic dialkylamide solvent further comprises di-N-propyl acetamide.

### Claim 5 (depends on 1)

The process of claim 1 wherein the at least one aprotic dialkylamide solvent further comprises N-formyl morpholine.

### Claim 6 (depends on 1)

The process of claim 1 wherein the at least one aprotic dialkylamide solvent further comprises di-N-butylacetamide.

### Claim 7 (depends on 1)

The process of claim 1 wherein the at least one aprotic dialkylamide solvent further comprises N-propionyl morpholine.

### Claim 8 (depends on 1)

A polyamideimide product produced by the process of claim 1.

### Claim 9 (depends on 1)

The process of claim 1, further comprising:
reacting a diisocyanate with a trimellitic anhydride (TMA) in the presence of the at least one aprotic dialkylamide solvent.

### Claim 10 (depends on 1)

The method of claim 1, wherein a molar ratio of a total amount of the at least one aprotic dialkylamide solvent to a total amount of other process co-solvents is approximately 78:22.

### Claim 11 (depends on 1)

The method of claim 1, wherein the diisocyanate is 4,4′-methylene diphenyldiisocyanate (MDI).

### Claim 12 (depends on 9)

A polyamideimide product produced by the process of claim 9.

### Claim 13

A process for producing polyamideimide comprising using at least one aprotic dialkylamide solvent, wherein the at least one aprotic dialkylamide solvent includes N-acetyl morpholine, diethyl acetamide, di-N-propyl acetamide, N-formyl morpholine, diacetylpiperazine, N,N-diisopropylacetamide, di-N-butylacetamide or N-propionyl morpholine;
wherein a molar ratio of the at least one aprotic dialkylamide solvent to other process co-solvents is approximately 78:22; and
wherein the other process co-solvents are selected from the group consisting of water, o-xylene, triethylamine, dimethylethanolamine, morpholine, N-methylmorpholine, acetone, trimethylamine, tripropylamine, diethylamine, diisopropylamine, and caprolactam.