# US 2023/0348786 A1 · Flame retardant phosphonium dicarboxylic acid ionic liquid compound, flame retardant synthetic polymer, fiber and fabric containing the same

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- Number: US 2023/0348786 A1
- Document ID: US20230348786A1
- Status: Published application
- Kind: A1
- Application number: 18/121,068
- Filed: 2023-03-14
- Published: 2023-11-02
- Earliest claimed: 2022-03-18
- Assignees: Materials Modification, Inc.
- Applicants: Materials Modification Inc.
- Inventors: KRISHNASWAMY KASTHURI RANGAN; TIRUMALAI SRINIVAS SUDARSHAN
- Web page: https://patentgrep.com/patent/US20230348786A1

## CPC

- C09K 21/14: Macromolecular materials
- C07F 9/5407: {Acyclic saturated phosphonium compounds}
- C08G 69/265: {from at least two different diamines or at least two different dicarboxylic acids}
- C08G 69/42: Polyamides containing atoms other than carbon, hydrogen, oxygen, and nitrogen (C08G69/12, C08G69/32 take precedence)
- C09D 5/18: Fireproof paints {including high temperature resistant paints}
- C09D 177/06: Polyamides derived from polyamines and polycarboxylic acids (C09D177/10 takes precedence)
- C08K 5/50: Phosphorus bound to carbon only
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07F: ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM (metal-containing porphyrins C07D487/22)
- 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)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

A phosphorus-containing ionic liquid, a phosphorus-containing a flame retardant additive, and a preparation method thereof are provided. Also provided are co-monomer salt compositions for flame retardant polymers. Also provided are polymers that comprise the phosphorus-containing flame retardant ionic liquid or flame retardant co-monomer salt. The resin composition may be used to make various articles, including fibers, fabrics, and yarns.

## Claims

### Claim 1

A flame retardant ionic liquid compound represented by the structure of Formula 1:
wherein
X is a chemical moiety comprising a dicarboxylic acid group selected from the group consisting of oxalic acid (ethanedioic acid), malonic acid (propanedioic acid), succinic acid (butanedioic acid), glutaric acid (pentanedioic acid), adipic acid (hexanedioic acid), pimelic acid (heptanedioic acid), suberic acid (octanedioic acid), azelaic acid (nonanedioic acid), sebacic acid (decanedioic acid), undecanedioic acid, dodecanedioic acid, brassylic acid (tridecanedioic acid), thapsic acid (hexadecanedioic acid), heneicosanedioic acid, docosanedioic acid, triacontanedioic acid, and combinations thereof;
R1 is selected from the group consisting of an alkyl group, an aryl group and combinations thereof;
R2 is selected from the group consisting of an alkyl group, an aryl group and combinations thereof;
R3 is selected from the group consisting an alkyl group, an aryl group and combinations thereof;
A- is an anion selected from the group consisting of bromide, chloride, iodide, adipate, and succinate, oxalate, malonate, glutarate, pimelicate, subericate (octanedioic carboxylic anion), and combinations thereof;
wherein the alkyl group is CnH2n+1; and wherein n = 1 to 20.

### Claim 2

A flame retardant intermediate compound represented by structure of Formula 2:
wherein
X is a chemical moiety comprising a dicarboxylic acid group selected from the group consisting of oxalic acid (ethanedioic acid), malonic acid (propanedioic acid), succinic acid (butanedioic acid), glutaric acid (pentanedioic acid), adipic acid (hexanedioic acid), pimelic acid (heptanedioic acid), suberic acid (octanedioic acid), azelaic acid (nonanedioic acid), sebacic acid (decanedioic acid), undecanedioic acid, dodecanedioic acid, brassylic acid (tridecanedioic acid), thapsic acid (hexadecanedioic acid), heneicosanedioic acid, docosanedioic acid, triacontanedioic acid, and combinations thereof;
R1 is selected from the group consisting of an alkyl group, an aryl group and combinations thereof;
R2 is selected from the group consisting of an alkyl group, an aryl group and combinations thereof;
R3 is selected from the group consisting an alkyl group, an aryl group and combinations thereof;
A- is an anion selected from the group consisting of bromide, chloride, iodide, adipate, and succinate, oxalate, malonate, glutarate, pimelicate, subericate (octanedioic carboxylic anion), and combinations thereof;
wherein the alkyl group is CnH2n+1; and wherein n = 1 to 20.

### Claim 3 (depends on 1)

A flame retardant polymer comprising a polymerization product of the flame retardant ionic liquid compound of claim 1.

### Claim 4 (depends on 3)

The flame retardant polymer of claim 3 selected from the group consisting of a polyamide, a polyester, a polyurethane, a polyimide and combinations thereof.

### Claim 5 (depends on 2)

A flame retardant polyamide comprising a polymerization product of the flame retardant intermediate compound of claim 2.

### Claim 6 (depends on 2)

A flame retardant intermediate compound of claim 2 represented by the structure of Formula 3:
.

### Claim 7 (depends on 2)

A flame retardant intermediate compound of claim 2 represented by the structure of Formula 4:
.