# US 2014/0155569 A1 · Flame-Retardant Derivatives

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- Number: US 2014/0155569 A1
- Document ID: US20140155569A1
- Status: Published application
- Kind: A1
- Application number: 14/115,165
- Filed: 2012-04-30
- Published: 2014-06-05
- Earliest claimed: 2011-05-02
- Assignees: University of Massachusetts
- Inventors: Jayant Kumar; E. Bryan Coughlin; Todd Emrick; Bon-Cheol Ku; Sethumadhavan Ravichandran; Subhalakshmi Nagarajan; Ramaswamy Nagarajan; Weeradech Kiratitanavit
- Web page: https://patentgrep.com/patent/US20140155569A1

## CPC

- C08G 8/02: of ketones
- C07C 49/83: polycyclic
- C07C 49/84: containing ether groups, [IMAGE cpc-sch-C07C-0958.gif] groups,[IMAGE cpc-sch-C07C-0959.gif] groups, or[IMAGE cpc-sch-C07C-0960.gif] groups
- C12P 7/26: Ketones
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C12P: FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE {(brewing of beer C12C; producing vinegar C12J; producing specific peptides or proteins C07K; producing enzymes C12N9/00; DNA or RNA concerning genetic engineering, vectors, e.g. plasmids, or their isolation, preparation or purification C12N15/00; measuring or testing processes involving enzymes or microorganisms C12Q; measuring or testing processes involving nucleic acid amplification reactions C12Q1/6844; fermentation processes to form a food composition, A21 or A23; compounds in general, see the relevant compound class, e.g. C01, C07)}

## Abstract

A chemical compound of structural formula (I) useful in preparation of flame retardant materials is disclosed. Homopolymer, and copolymers of a compound of formula (I), as well as methods of preparing said homo- and copolymers are also disclosed. Polymers described herein advantageous possess low heat release capacities and high char yields.

## Claims

### Claim 1

A chemical compound of structural formula (I):
wherein:
R1, R2, R3, R4, R5 and R6 each independently is selected from —H, —OH, a C1-C8 alkoxy, a C1-C15 alkyl, a C2-C15 alkenyl, or a C2-C15 alkynyl; and
n is 0 or 1;
provided that:
(1) at least one of R1, R2, R3, R4, R5 and R6 is —OH;
(2) when R1 and R2 each is —OH, then at least one of R3, R4, R5 and R6 is not —H; and
(3) when R1 is —OH and R2 is —OCH3, then at least one of R3, R4, R5 and R6 is not —H.

### Claim 2 (depends on 1)

The compound of claim 1, represented by a structural formula selected from formulas (II), (III) and (IV):

### Claim 3 (depends on 1)

The compound of claim 1, wherein R1 is —OH and R2 is —OH or —OCH3.

### Claim 4 (depends on 3)

The compound of claim 3, wherein R3, R4, R5 and R6 each is independently —H or a C1-C8 alkyl.

### Claim 5 (depends on 1)

The compound of claim 1, wherein:
R1 is —OH, R2 is —OH, and R3, R4, R5, and R6 each is each independently a C5-C8 alkyl, or
R1 is —OH, R2 is —OCH3, and R3, R4, R5, and R6 each is each independently a C5-C8 alkyl.

### Claim 6 (depends on 1)

The compound of claim 1, wherein:
R1 is —OH, R3, R4, R5, and R6 each is —CH3; and
R2 is —OH or —OCH3.

### Claim 7

A poly(deoxybenzoin) homopolymer of any one of the monomers of structural formula (I):
wherein:
R1, R2, R3, R4, R5 and R6 each independently is selected from —H, —OH, a C1-C8 alkoxy, or a C1-C15 alkyl; and
n is 0 or 1,
provided that at least one of R1, R2, R3, R4, R5 and R6 is —OH.

### Claim 8 (depends on 7)

The homopolymer of claim 7, wherein the monomer of structural formula (I) is represented by a structural formula selected from formulas (II), (III) and (IV):

### Claim 9 (depends on 7)

The homopolymer of claim 7, wherein R1 is —OH and R2 is —OH or —OCH3.

### Claim 10 (depends on 9)

The homopolymer of claim 9, wherein
R3, R4, R5 and R6 each is independently —H or a C1-C8 alkyl.

### Claim 11 (depends on 7)

The homopolymer of claim 7, wherein:
R1 is —OH, R3, R4, R5, and R6 each is independently a C5-C8 alkyl, and R2 is —OH, or —OCH3.

### Claim 12 (depends on 7)

The homopolymer of claim 7, wherein:
R1 is —OH, and R3, R4, R5, and R6 each is —CH3, and R2 is —OH or —OCH3.

### Claim 13 (depends on 7)

The homopolymer of claim 7, wherein:
R1 is —OH, and R3, R4, R5, and R6 each is —H, and R2 is —OH or —OCH3.

### Claim 14

A poly(deoxybenzoin) copolymer of at least one of the monomers of structural formula (I) and at least one additional monomer:
wherein:
R1, R2, R3, R4, R5 and R6 each independently is selected from —H, —OH, a C1-C8 alkoxy, a C1-C15 alkyl, a C2-C15 alkenyl or a C2-C15 alkynyl; and
n is 0 or 1,
provided that:
(1) at least one of R1, R2, R3, R4, R5 and R6 is —OH; and
(2) when n=1 and when R1 and R2 each is —OH, then at least one of R3, R4, R5 and R6 is not —H.

### Claim 15 (depends on 14)

The copolymer of claim 14, wherein the monomers of structural formula (I) is represented by a structural formula selected from formulas (II), (III) and (IV):

### Claim 16 (depends on 14)

The copolymer of claim 14, wherein R1 is —OH and R2 is —OH or —OCH3.

### Claim 17 (depends on 16)

The copolymer of claim 16, wherein R3, R4, R5 and R6 each is independently —H or a C1-C8 alkyl.

### Claim 18 (depends on 14)

The copolymer of claim 14, wherein:
R1 is —OH, R3, R4, R5, and R6 each is independently a C5-C8 alkyl, and R2 is —OH or —OCH3.

### Claim 19 (depends on 14)

The copolymer of claim 14, wherein:
R1 is —OH, R3, R4, R5, and R6 each is —CH3, and R2 is —OH or —OCH3.

### Claim 20 (depends on 14)

The copolymer of claim 14, wherein R1 is —OH, R2 is —OCH3, and R3, R4, R5, and R6 each is —H.

### Claim 21 (depends on 14)

The copolymer of claim 14, wherein the at least one additional monomer is a compound of formula (V) or formula (VI):
wherein R, for each occurrence independently, is a C1-C15 alkyl, a C2-C15 alkenyl or a C2-C15 alkynyl.

### Claim 22 (depends on 14)

The copolymer of claim 14, wherein the at least one additional monomer is selected from the group consisting of phenol, ethylphenol, phenylphenol, 3-(4-hydroxyphenyl)-1-proponal, 4-hydroxyphenylaceticacid, cardanol, and 3-pentadecylphenol.

### Claim 23

A method of producing a poly(deoxybenzoin) homopolymer of any one of the monomers of structural formula (I):
wherein:
R1, R2, R3, R4, R5 and R6 each independently is selected from —H, —OH, a C1-C8 alkoxy, a C1-C8 alkyl, a C1-C8 alkenyl or a C1-C8 alkynyl,
provided that at least one of R1, R2, R3, R4, R5 and R6 is —OH, comprising the step of:
synthesizing a covalent bond between at least two monomers of structural formula (I) to produce the poly(deoxybenzoin) homopolymer.

### Claim 24 (depends on 23)

The method of claim 23, wherein the monomers of structural formula (I) is represented by a structural formula selected from formulas (II), (III) and (IV):

### Claim 25 (depends on 23)

The method of claim 23, wherein synthesizing the covalent bond between the at least two monomers of structural formula (I) includes contacting the at least two monomers of structural formula (I) with an enzyme.

### Claim 26 (depends on 25)

The method of claim 25, wherein the enzyme is a heme-containing enzyme or a metalloporphyrin-containing enzyme.

### Claim 27 (depends on 25)

The method of claim 25, wherein the enzyme is a peroxidase.

### Claim 28 (depends on 23)

The method of claim 23, wherein synthesizing the covalent bond between the at least two monomers of structural formula (I) includes contacting the at least two monomers of structural formula (I) with chemical oxidation catalyst.

### Claim 29 (depends on 26)

The method of claim 26, wherein the chemical oxidation catalyst is selected from ferric chloride, ammonium persulfate and potassium ferricyanide.

### Claim 30

A method of producing a poly(deoxybenzoin) copolymer of at least one of the monomers of structural formula (I) and at least one additional monomer:
wherein:
R1, R2, R3, R4, R5 and R6 each independently is selected from —H, —OH, a C1-C8 alkoxy, a C1-C15 alkyl, a C2-C15 alkenyl or a C2-C15 alkynyl; and
n is 0 or 1;
provided that:
(1) at least one of R1, R2, R3, R4, R5 and R6 is —OH; and
(2) when n=1 and when R1 and R2 each is —OH, then at least one of R3, R4, R5 and R6 is not —H,
comprising the step of:
synthesizing a covalent bond between at least one monomer of structural formula (I) and at least one additional monomer to produce the poly(hydroxydeoxybenzoin) copolymer.

### Claim 31 (depends on 30)

The method of claim 30, wherein the monomers of structural formula (I) is represented by a structural formula selected from formulas (II), (III) and (IV):

### Claim 32 (depends on 30)

The method of claim 30, wherein the covalent bond between the at least one monomer of structural formula (I) and the at least one additional monomer includes contacting the at least one monomer of structural formula (I) and the at least one additional monomer with an enzyme.

### Claim 33 (depends on 32)

The method of claim 32, wherein the enzyme is a heme-containing or a metalloporphyrin-containing enzyme.

### Claim 34 (depends on 32)

The method of claim 32, wherein the enzyme is a peroxidase.

### Claim 35 (depends on 30)

The method of claim 30, wherein synthesizing the covalent bond between the at least one monomer of structural formula (I) and the at least one additional monomer includes contacting the at least one monomer of structural formula (I) and the at least one additional monomer with a chemical oxidation catalyst.

### Claim 36 (depends on 35)

The method of claim 35, wherein the chemical oxidation catalyst is selected from ferric chloride, ammonium persulfate and potassium ferricyanide.

### Claim 37

An article of manufacture, comprising a poly(deoxybenzoin) homopolymer of any one of the monomers of structural formula (I):
wherein:
R1, R2, R3, R4, R5 and R6 each independently is selected from —H, —OH, a C1-C8 alkoxy, a C1-C15 alkyl, a C2-C15 alkenyl or a C2-C15 alkynyl; and
n is 0 or 1;
provided that at least one of R1, R2, R3, R4, R5 and R6 is —OH.

### Claim 38

An article of manufacture, comprising a poly(deoxybenzoin) copolymer of at least one of the monomers of structural formula (I) and at least one additional monomer:
wherein:
R1, R2, R3, R4, R5 and R6 each independently is selected from —H, —OH, a C1-C8 alkoxy, a C1-C15 alkyl, a C2-C15 alkenyl or a C2-C15 alkynyl; and
n is 0 or 1;
provided that:
(1) at least one of R1, R2, R3, R4, R5 and R6 is —OH; and
(2) when R1 and R2 each is —OH, then at least one of R3, R4, R5 and R6 is not —H.

### Claim 39 (depends on 38)

The article of claim 38, wherein the at least on additional monomer is selected from the group consisting of:
formula (V) or formula (VI):
wherein R, for each occurrence independently, is a C1-C15 alkyl, a C1-C15 alkenyl or a C1-C15 alkynyl.