Flame retardant for polyurethanes

• US 4,564,468 A
• Filed: 12/12/1984
• Issued: 01/14/1986
• Est. Priority Date: 09/17/1981
• Status: Expired due to Fees

• Current Assignee: Albemarle Corporation
• Original Assignee: Ethyl Corporation (Newmarket Corporation)
• Inventors: Barda, Henry J.
• Primary Examiner(s): Lovering, Richard D.
• Application Number:
  US06/680,930
• Time in Patent Office: 398 Days
• Field of Search: 252/609, 260/DIG. 24, 428/921
• US Class Current: 252/609
• CPC Class Codes: C08G 18/3846 containing imide groups C08G18/3821 takes precedence
• CPC Class Codes: Y10S 260/24 Flameproof
• CPC Class Codes: Y10S 428/921 Fire or flameproofing

Abstract

A reactive fire retardant mixture useful in the preparation of polyurethane foams. The mixture contains a halogenated imide-containing polyol having the formula: ##STR1## and the corresponding ether having the formula: ##STR2## wherein R is a hydrocarbon group having the valance n+2 and is selected from the group consisting of benzene groups, naphthalene groups and alicyclic hydrocarbon groups containing 5 to 10 carbon atoms, R'"'"' is an aliphatic hydrocarbon group containing 3-12 carbon atoms, X is selected from the group consisting of bromine and chlorine, n is an integer from 1-6 and p is an integer from 2-6. They are prepared by reacting an alcohol (e.g. isopropyl alcohol), a halogenated dicarboxylic anhydride (e.g. tetrabromophthalic anhydride) and an aminopolyol (e.g. 2-amino-2-ethyl-1,3-propanediol).

Claims

1. A reactive flame retardant mixture comprising about 1-99 weight percent of a halogenated imide-containing polyol having the formula:

##STR21## and about 99-1 weight percent of the corresponding ether having the formula;

##STR22## wherein R is a hydrocarbon group having the valence n+2 and is selected from the group consisting of benzene groups, naphthalene groups and alicyclic hydrocarbon groups containing 5 to 10 carbon atoms, R'"'"' is an aliphatic hydrocarbon group containing 3-12 carbon atoms, X is selected from the group consisting of bromine and chlorine, n is an integer from 1-6 and p is an integer from 2-6.

2. A reactive flame retardant mixture, as recited in claim 1, wherein R'"'"' is an aliphatic hydrocarbon group containing 5 carbon atoms and p is 2.

3. A reactive flame retardant mixture, as recited in claim 2, wherein R is benzene, X is bromine and n is 4.

4. A reactive flame retardant mixture, as recited in claim 3, wherein the halogenated imide-containing polyol has the formula:

##STR23## and the corresponding ether has the formula;

##STR24##

5. A reactive flame retardant mixture, as recited in claim 2, wherein R is 5-norbornene, X is chlorine and n is 6.

6. A reactive flame retardant mixture, as recited in claim 5, wherein the halogenated imide-containing polyol has the formula:

##STR25## and the corresponding ether has the formula;

##STR26##

7. A process for preparing a reactive flame retardant mixture, said process comprising reacting at a temperature of about 50°

-350°

C.

(a) about one mole of a halogenated dicarboxylic anhydride compound having the structure;

##STR27## wherein R is a hydrocarbon group having the valence n+2 and is selected from the group consisting of benzene groups, naphthalene groups and alicyclic hydrocarbon groups containing 5 to 10 carbon atoms, X is selected from the group consisting of bromine and chlorine and n is an integer from 1 to 6,

(b) about 0.8-50 moles of an alcohol containing 1-10 carbon atoms and

(c) about 0.5-2.5 moles of an aminopolyol having the structure;

space="preserve" listing-type="equation">H.sub.2 N--R'"'"'--OH).sub.p

wherein R'"'"' is an aliphatic hydrocarbon group containing 2-6 carbon atoms having the valence p+1 and p is an integer from 2-6.

8. A process for preparing a reactive flame retardant mixture, as recited in claim 7, wherein said alcohol is isopropyl alcohol, said halogenated dicarboxylic anhydride is tetrabromophthalic anhydride and said aminopolyol is 2-amino-2-ethyl-1,3-propanediol.

9. A process for preparing a reactive flame retardant mixture, said process comprising reacting at a temperature of about 50°

-350°

C.

(a) about one mole of a halogenated dicarboxylic anhydride compound having the structure;

##STR28## wherein R is a hydrocarbon group having the valence n+2 and is selected from the group consisting of benzene groups, naphthalene groups and alicyclic hydrocarbon groups containing 5 to 10 carbon atoms, X is selected from the group consisting of bromine and chlorine and n is an integer from 1 to 6 and

(b) about 0.8-50 moles of an alcohol containing 1-10 carbon atoms to form an acid-ester intermediate and reacting said intermediate with

(c) about 0.5-2.5 moles of an aminopolyol having the structure;

space="preserve" listing-type="equation">H.sub.2 N--R'"'"'--OH).sub.p

wherein R'"'"' is an aliphatic hydrocarbon group containing 2-6 carbon atoms having the valence p+1 and p is an integer from 2-6.

10. A process for preparing a reactive flame retardant mixture, as recited in claim 9, wherein said alcohol is isopropyl alcohol, said halogenated dicarboxylic anhydride is tetrabromophthalic anhydride and said aminopolyol is 2-amino-2-ethyl-1,3-propanediol.