Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From phenol – phenol ether – or inorganic phenolate
Reexamination Certificate
1999-12-22
2001-05-15
Boykin, Terressa M. (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From phenol, phenol ether, or inorganic phenolate
Reexamination Certificate
active
06232427
ABSTRACT:
BACKGROUND OF THE INVENTION
The invention relates to methods of making esters and the use of these esters in polymer compositions.
Tetrabromophthalic anhydride can be reacted with an alcohol to form tetrabromophthalate. At reaction temperatures, tetrabromophthalic anhydride can undergo decarboxylation. Sulfuric acid, which is often used during synthesis of the tetrabromophthalic anhydride, can also be used to reduce decarboxylation of the anhydride. However, the sulfuric acid can degrade the alcohol used during esterification, potentially resulting in reduced yield of tetrabromophthalate and decreased yield of recycled alcohol. Therefore, the alcohol and tetrabromophthalic anhydride are usually reacted in the presence of a neutralizing agent. Such neutralizing agents include, for example, sodium acetate and potassium acetate.
SUMMARY OF THE INVENTION
The invention relates to methods of esterifying carboxylated, halogenated aromatic compounds to form halogenated aromatic esters. These methods can result in good purity of the final product and high yields of the desired halogenated aromatic esters. In addition, the methods can reduce costs by using the reactants, such as alcohols, in a more efficient manner.
The invention also relates to the use of the halogenated aromatic esters in polymer compositions. These polymer compositions can offer benefits including flame resistance and smoke suppression.
In one aspect, the invention features a method of esterifying a carboxylated, halogenated aromatic compound, such as a tetrabromophthalate. The method includes contacting the carboxylated, halogenated aromatic compound with an alcohol and a sulfuric acid deactivating compound capable of forming a water insoluble sulfate compound.
As used herein, “halogenated aromatic compound” refers to an aromatic compound that has at least one halogen atom directly bonded to an aromatic carbon atom.
As used herein, “carboxylated, halogenated aromatic compound” denotes a halogenated aromatic compound that has at least one carboxyl carbon atom directly bonded to an aromatic carbon atom. Typically, carboxylated, halogenated aromatic compounds are halogenated aromatic carboxylic acids or halogenated aromatic carboxylic anhydrides.
As used herein, “sulfuric acid deactivating compound capable of forming a water insoluble sulfate compound” refers to a compound that can react with sulfuric acid to reduce the concentration of sulfuric acid and form a sulfate-containing compound that has a solubility product in water of less than about 1×10
−4
when measured at a temperature of about 25° C.
In another aspect, the invention features a method of esterifying tetrabromophthalic anhydride. The method includes contacting tetrabromophthalic anhydride with an alcohol in the presence of barium acetate.
In some embodiments, the method can also include contacting an esterification catalyst with the reactants to increase the rate of esterification. In these embodiments, an esterification catalyst deactivating compound can be added after formation of the halogenated aromatic ester to prevent the esterification catalyst from catalyzing hydrolysis of the halogenated aromatic ester.
In certain embodiments, the method can also include contacting an anti-oxidant to reduce color formation of the halogenated aromatic ester.
In yet another aspect, the invention features a polymer composition that includes a halogenated aromatic ester made according to one of the above-noted methods.
In yet a further aspect, the invention features a polymer composition that includes a polyvinyl chloride, a pentaerythritol ester, aluminum trihydrate, an antimony trioxide flame retardant, an isodecyl diphenyl phosphate plasticizer, a zinc borate flame retardant and a halogenated aromatic ester including at most about 0.1 weight percent of ether compounds. The halogenated aromatic ester can be derived from a linear alcohol.
As used herein, the term “linear alcohol” refers to alcohols with hydrocarbon chains that are noncyclic and nonbranched.
In other aspects, the invention features a polymer composition that includes an aromatic ester derived from a non-linear alcohol or a mixture of aromatic esters that are derived from both linear alcohols and non-linear alcohols.
As used herein, the term “non-linear alcohol” refers to alcohols that are not linear alcohols.
The halogenated aromatic ester(s) included in the polymer compositions of the invention can include less than about 0.1 weight percent (e.g., less than about 0.05 weight percent) of ether compounds.
The halogenated aromatic ester(s) included in the polymer compositions of the invention can include less than about 10 weight percent (e.g., less than about five weight percent or less than about two weight percent) of undesired halogenated aromatic esters.
In yet another aspect, the invention features a plasticizer, which when used, e.g., in PVC compositions, can provide the composition with good performance at low temperature. The plasticizer includes a brominated aromatic ester and a chlorinated aromatic ester, typically with the latter in sufficient amounts to make the plasticizer a liquid at room temperature. Therefore, the plasticizer can be handled easily during production and well blended with the composition. The preferred brominated aromatic ester is a tetrabromophthalate, and the preferred chlorinated aromatic ester is a tetrachlorophthalate. Such compositions are useful as flame retardants and are good for cable jacketing and wire insulation.
Other features and advantages of the invention will be apparent from the description of the preferred embodiments.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
The halogenated aromatic esters are made by reacting a carboxylated, halogenated aromatic compound with an alcohol in the presence of a sulfuric acid deactivating compound capable of forming a water insoluble sulfate compound.
Examples of carboxylated, halogenated aromatic compounds include monobromophthalic acid, dibromophthalic acid, tribromophthalic acid, tetrabromophthalic acid, pentabromobenzoic acid, monochlorophthalic acid, dichlorophthalic acid, trichlorophthalic acid, tetrachlorophthalic acid, pentachlorobenzoic acid, monobromophthalic anhydride, dibromophthalic anhydride, tribromophthalic anhydride, tetrabromophthalic anhydride, monochlorophthalic anhydride, dichlorophthalic anhydride, trichlorophthalic anhydride and tetrachlorophthalic anhydride.
Examples of sulfuric acid deactivating compounds include barium acetate, barium bromide, barium propionate, barium butyrate, barium chlorate, barium chloride, barium dithionate, barium formate, barium hydroxide, barium iodide, barium nitrate, barium nitrite, barium oxide, barium hypophosphite, barium salicylate, barium peroxydisulfate, barium monosulfide, barium disulfide, barium trisulfide, lead acetate, lead chlorate, lead perchlorate, lead citrate, lead ethylsulfate, lead formate, lead butyrate, lead lactate, lead nitrite, lead nitrate, lead peroxyl disulfate, lead dithionate, mercury chlorate, strontium acetate, strontium bromate, strontium bromite, strontium chlorate, strontium perchlorate, strontium chloride, strontium formate, strontium hydroxide, strontium iodide, strontium lactate, strontium nitrate, strontium nitrate, strontium oxide, strontium salicylate, strontium monosulfite, strontium trisulfite, strontium tetrasulfite, strontium dithionate, calcium acetate, calcium benzoate, calcium bromide, calcium bromate, calcium butyrate, calcium chlorate, calcium perchlorate, calcium chloride, calcium formate, calcium fumarate, calcium gluconate, calcium iodide, calcium butyrate, calcium lactate, calcium valerate, calcium nitrate, calcium nitrite, calcium hypophosphite, calcium propionate, calcium salicylate and calcium dithionate.
The alcohol can be a straight-chained alcohol, a branched alcohol, a cyclic alcohol, a saturated alcohol, an unsaturated alcohol, a substituted alcohol and/or an unsubstituted alcohol. In addition, the alcohol can include more than one alcoholic hydroxyl group, such as polyols and glycols. Furthermor
Buono John A.
Cobb Maryellen
Tao Tao T.
Boykin Terressa M.
Fish & Richardson P.C.
Teknor Apex Company
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