Tetrabromophthalic diester flame retardants and their production

Patent metadata

Field	Value
Publication number	US-9227908-B2
Application number	US-98046910-A
Country	US
Kind code	B2
Filing date	Dec 29, 2010
Priority date	Jan 7, 2010
Publication date	Jan 5, 2016
Grant date	Jan 5, 2016

Abstract

In a process for producing a tetrabromophthalic diester composition, a liquid reaction mixture is prepared comprising tetrabromophthalic anhydride (TBPA), a C 2 to C 6 polyhydric aliphatic alcohol (PAA) and an alkylene oxide (AO) selected from the group consisting of ethylene oxide and propylene oxide, said reaction mixture being substantially free of an organic solvent. While agitating the reaction mixture, the temperature of the reaction mixture is raised to at least 50° C. to allow the TBPA to react with the PAA and AO to produce a diester composition. The reaction is terminated when the diester composition has an acid value equal to or less than 0.25 mg KOH/gm of the diester composition.

First claim

We claim:

1. A process for producing a tetrabromophthalic diester diol composition, the process comprising:
(a) preparing a liquid reaction mixture comprising tetrabromophthalic anhydride (TBPA), from about 1.5 moles to about 2.0 moles of propylene oxide per mole of TBPA, and from about 1.5 to about 2.0 moles of diethylene glycol per mole of TBPA, said reaction mixture being substantially free of an organic solvent; then,
(b) while agitating the reaction mixture, raising the temperature of the reaction mixture to between about 60° C. and about 65° C. to initiate an exothermic reaction of TBPA with the propylene oxide and diethylene glycol to produce the diester diol composition, wherein the reaction temperature is kept at or below 120° C.; and
(c) terminating the reaction when the diester diol composition has an acid value equal to or less than 0.25 mg KOH/gm and removing volatiles under vacuum to yield the tetrabromophthalic diester diol composition,
wherein the tetrabromophthalic diester diol composition has a viscosity of about 15,000 to about 40,000 cps at 25° C. and is the reaction product of tetrabromophthalic anhydride (TBPA), propylene oxide and diethylene glycol, wherein the tetrabromophthalic diester diol has a formula of

 where n is from about 1 to about 5.

2. The process of claim 1 , wherein the reaction mixture also comprises potassium hydroxide in an amount between about 0.001 to about 0.05 mole per mole of TBPA.

3. The process of claim 1 , wherein the reaction is terminated when the diester diol composition has an acid value between about 0.04 and about 0.10 mg KOH/gm.

4. A process for producing a tetrabromophthalic diester diol composition, the process comprising:
(a) preparing a liquid reaction mixture comprising tetrabromophthalic anhydride (TBPA), propylene oxide in an amount that is 20 to 35% of the total amount ranging from about 1.5 moles to about 2.0 moles of propylene oxide per mole of TBPA, from about 1.5 to about 2.0 moles of diethylene glycol per mole of TBPA, and between about 0.001 to about 0.05 moles of potassium hydroxide per mole of TBPA, said reaction mixture being substantially free of an organic solvent; then,
(b) while agitating the reaction mixture, raising the temperature of the reaction mixture to between about 60 ° C. and about 65° C. to initiate an exothermic reaction of TBPA with the propylene oxide and diethylene glycol and then adding the remainder of the about 1.5 moles to about 2.0 moles of propylene oxide per mole of TBPA to the reaction mixture to produce the diester diol composition, wherein the reaction temperature is kept at or below 120 ° C.; and
(c) terminating the reaction when the diester diol composition has an acid value equal to or less than 0.25 mg KOH/gm and removing volatiles under vacuum to yield the tetrabromophthalic diester diol composition,
wherein the tetrabromophthalic diester composition has a viscosity of about 15,000 to about 40,000 cps at 25 ° C. and is the reaction product of tetrabromophthalic anhydride (TBPA), propylene oxide and diethylene glycol, wherein the tetrabromophthalic diester diol has a formula of

where n is from about 1 to about 5.

Assignees

• Bartley David W
• Pickering Roy
• Ray Thomas G
• Chemtura Corp

Inventors

• Bartley David W
• Pickering Roy
• Ray Thomas G

Classifications

• C07C69/76 Primary

  Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring · CPC title

• C08K5/0066

  Flame-proofing or flame-retarding additives · CPC title

• C08K5/0008

  Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59 · CPC title

• C08K5/12 Primary

  of cyclic polycarboxylic acids · CPC title

• C08L75/04

  Polyurethanes · CPC title