# US 2020/0399540 A1 · Brominated flame-retardant tetrazines

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- Number: US 2020/0399540 A1
- Document ID: US20200399540A1
- Status: Published application
- Kind: A1
- Application number: 16/445,541
- Filed: 2019-06-19
- Published: 2020-12-24
- Earliest claimed: 2019-06-19
- Assignees: International Business Machines Corporation
- Applicants: International Business Machines Corporation
- Inventors: Brandon M. Kobilka; Jason T. Wertz; Scott B. King; Jacob Porter
- Web page: https://patentgrep.com/patent/US20200399540A1

## CPC

- C09K 21/10: containing nitrogen
- C07D 257/08: Six-membered rings
- C08K 5/3477: Six-membered rings
- C08K 5/3492: Triazines
- C08K 5/0066: {Flame-proofing or flame-retarding additives}
- C08K 5/03: aromatic {, e.g. C6H5-CH2-Cl}
- C09K: MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08K: Use of inorganic or non-macromolecular organic substances as compounding ingredients (paints, inks, varnishes, dyes, polishes, adhesives C09)

## Abstract

A flame-retardant compound, a process for forming a flame-retardant compound, and an article of manufacture. The flame-retardant compound includes a tetrazine moiety and at least one ligand comprising a brominated moiety. The process includes providing starting materials, which include a nitrile compound, a bromine source, and hydrazine. The process also includes reacting the starting materials to form a tetrazine flame retardant. The article of manufacture includes a polymer and a flame-retardant compound having a tetrazine moiety and at least one ligand comprising a brominated moiety.

## Claims

### Claim 1

A flame-retardant compound, comprising:
a tetrazine moiety; and
at least one ligand comprising a brominated moiety.

### Claim 2 (depends on 1)

The flame-retardant compound of claim 1, wherein the brominated moiety is a hexabromocyclododecyl moiety.

### Claim 3 (depends on 2)

The flame-retardant compound of claim 2, wherein the at least one ligand has a formula selected from the group consisting of:
wherein each M represents the hexabromocyclododecyl moiety, and wherein each dashed line represents a bond to a carbon atom in the tetrazine moiety.

### Claim 4 (depends on 1)

The flame-retardant compound of claim 1, wherein the brominated moiety comprises a brominated phenyl group.

### Claim 5 (depends on 4)

The flame-retardant compound of claim 4, wherein the at least one ligand has a formula selected from the group consisting of:
wherein each dashed line represents a bond to a carbon atom in the tetrazine moiety.

### Claim 6

A process, comprising:
providing starting materials, the starting materials comprising:
a nitrile compound;
hydrazine; and
a bromine source;
reacting the starting materials to form a tetrazine flame retardant.

### Claim 7 (depends on 6)

The process of claim 6, wherein the bromine source is selected from the group consisting of elemental bromine and an organobromide compound.

### Claim 8 (depends on 6)

The process of claim 6, wherein the providing the starting materials comprises providing a nitrile-substituted hexabromocyclododecane.

### Claim 9 (depends on 6)

The process of claim 6, wherein the reacting the starting materials comprises:
reacting the nitrile compound with the hydrazine to form a tetrazine compound; and
reacting the tetrazine compound with the bromine source.

### Claim 10 (depends on 6)

The process of claim 6, wherein the reacting the starting materials comprises:
forming a brominated nitrile compound; and
reacting a brominated nitrile compound with the hydrazine.

### Claim 11 (depends on 6)

The process of claim 6, wherein the reacting the starting materials comprises a Williamson ether synthesis.

### Claim 12 (depends on 6)

The process of claim 6, further comprising incorporating the tetrazine flame retardant into a polymer.

### Claim 13 (depends on 12)

The process of claim 12, wherein the polymer is a polybutadiene.

### Claim 14 (depends on 12)

The process of claim 12, wherein the polymer is poly(ethylene-co-propylene-co-5-methylene-2-norbornene).

### Claim 15 (depends on 12)

The process of claim 12, wherein the incorporating comprises an inverse electron demand Diels-Alder reaction between the tetrazine flame retardant and a polymer having alkenyl moieties.

### Claim 16

An article of manufacture, comprising:
a polymer; and
a flame-retardant compound, comprising:
a tetrazine moiety; and
at least one ligand comprising a brominated moiety.

### Claim 17 (depends on 16)

The article of manufacture of claim 16, further comprising an electronic component.

### Claim 18 (depends on 16)

The article of manufacture of claim 16, wherein the polymer is a synthetic rubber.

### Claim 19 (depends on 16)

The article of manufacture of claim 16, wherein the polymer is a polybutadiene.

### Claim 20 (depends on 16)

The article of manufacture of claim 16, wherein the flame-retardant compound is covalently bound to the polymer.