BROMINE-FREE FIRE RETARDANT (FR) AGENTS CAPABLE OF USING A CYCLIZATION MECHANISM
Provided herein are fire retardant compounds capable of undergoing a cyclization reaction to provide an elimination product and a cyclization product, as described herein. Also provided are compositions, polymers and articles including a fire retardant compound, and processes for preparing the compositions and articles.
1 . A composition comprising at least one polymer; and
at least one fire retardant compound capable of undergoing a cyclization reaction to provide an elimination product and a cyclization product.
2 . The composition of claim 1 , wherein the polymer is a thermoset polymer or a thermoplastic polymer.
3 . The composition of claim 1 , wherein the fire retardant compound is halogen-free and phosphorous-free.
4 . The composition of claim 1 , wherein the fire retardant compound is a hydroxy-carboxylic acid, hydroxy ester, hydroxy-amide, hydoxy-amido-carboxylic acid, urea-carboxylic acid, urea-amino acid, urea-ester, amino-ester, amino-amide, amino acid, amino acid-amide, amino-amino acid, amino acid-ester, or a salt thereof.
5 . The composition of claim 1 , wherein the cyclization product comprises a five-member ring or a six-member ring.
6 . The composition of claim 1 , wherein the fire retardant compound is a compound of Formula (I):
or a salt thereof, wherein:
A is O, O − , NH or NR 5 ;
Y is (CH 2 ) 0-1 OH, (CH 2 ) 0.1 NH 2 , (CH 2 ) 0-1 NHR 6 , or (CH 2 ) 0-1 NR 6 R 7 ;
R 1 is H or a C 1 -C 6 hydrocarbon group optionally substituted with OH, NH 2 , carboxyl or a carboxylate; or, when A is O − , R 1 is a cation;
R 2a , R 3a , and R 4a are each independently H, a C 1 -C 6 hydrocarbon group, OH, or NH 2 ;
R 2b , R 3b , R 4b , R 5 , and R 6 are each independently H or a C 1 -C 6 hydrocarbon group; and
R 7 is H, a C 1 -C 6 hydrocarbon group, or C(═NH)NH 2 .
7 . The composition of claim 5 , wherein the fire retardant compound is:
8 . The composition of claim 1 , wherein the elimination product is not a halogen or halide.
9 . The composition of claim 1 , wherein the elimination product is at least one of H 2 O, NH 3 , ammonium ion, N 2 , alcohol, amine, and an amine salt.
10 . The composition of claim 1 , wherein one or more polymer is present in a concentration of about 5% to about 45% by weight based on the total composition.
11 . The composition of claim 1 , wherein the polymer is polyethylene (PE), polypropylene (PP), poly(butylene terephthalate) (PBT), poly(ethylene terephthalate) (PET), acrylonitrile-butadiene-styrene (ABS), high impact polystyrene (HIPS), or nylon.
12 . The composition of claim 1 , wherein the polymer is high impact polystyrene (HIPS).
13 . The composition of claim 1 , further comprising at least one filler, at least one additive, or both.
14 . (canceled)
15 . A method of making a fire-retardant composition, the method comprising:
combining at least one polymer and at least one fire retardant compound capable of undergoing a cyclization reaction to provide an elimination product and a cyclization product.
16 . The method of claim 15 , wherein the fire retardant compound is a hydroxy-carboxylic acid, hydroxy ester, hydroxy-amide, hydoxy-amido-carboxylic acid, urea-carboxylic acid, urea-amino acid, urea-ester, amino-ester, amino-amide, amino acid, amino acid-amide, amino-amino acid, amino acid-ester, or a salt thereof
17 . (canceled)
18 . The method of claim 16 , wherein the fire retardant compound is a compound of Formula (II), Formula (III) or Formula (IV):
19 . The method of claim 15 , further comprising:
heating the fire-retardant composition
extruding or molding the fire-retardant composition; and
cooling the extruded or molded composition.
20 . (canceled)
21 . (canceled)
22 . A method of protecting an article from fire, the method comprising:
exposing an article comprising:
at least one polymer; and
at least one fire retardant compound capable of undergoing a cyclization reaction to provide an elimination product and a cyclization product,
to flame or heat.
23 . The method of claim 22 , wherein the article displays improved fire and flame retardant characteristics compared to the same article not comprising the fire retardant compound.
24 . The method of claim 22 , wherein the article is an automotive, appliance, electric, electronic, toy, textile, carpet, upholstery, vehicle, or airplane, component.