Antistatic and antidust agents, compositions thereof, and methods of manufacture

1 . A method of making a quaternary onium aromatic sulfonate compound comprising:

preparing in a solvent a first solution comprising an aromatic sulfonic acid salt having the formula:

wherein “T” is an alkali metal, “a” is 0, 1 or 2, and “b” is 0, 1 or 2 with the proviso that (a+b) is an integer greater than or equal to 1; G 1 is an aromatic group; “E” is an ether linkage; each Y 1 independently comprises hydrogen, a monovalent hydrocarbon group, halogen, or OR, wherein “R” is a monovalent hydrocarbon group; “s”, “t”, and “u” each represents an integer equal to one, “X” is phosphorus and “q” represents any integer from and including zero through the number of positions on G 1 available for substitution;

contacting the first solution with an acidic medium to convert the alkali metal aromatic sulfonic acid salt to an aromatic sulfonic acid;

mixing the aromatic sulfonic acid with a quaternary compound;

extracting the aromatic sulfonic acid and quaternary salt mixture with an organic solvent to provide a second solution; and

evaporating the organic solvent from the second solution to obtain the quaternary onium aromatic sulfonate represented by the formula:

wherein each R 1 independently comprises aliphatic or aromatic, substituted or unsubstituted, carbocyclic or heterocyclic radicals, “a” has a value of 0, 1 or 2, and “b” has a value of 0, 1 or 2, with the proviso that (a+b) is greater than or equal to 1; G 1 is an aromatic group; “E” is an ether linkage; each Y 1 independently comprises hydrogen, a monovalent hydrocarbon group, halogen, or OR, wherein “R” is a monovalent hydrocarbon group; “s”, “t”, and “u” each represents an integer equal to one, “X” is phosphorus and “q” represents any integer from and including zero through the number of positions on G 1 available for substitution.

2 . The method of claim 1 , wherein said alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, and cesium.

3 . The method of claim 1 , further comprising maintaining a temperature at about 10° C. to about 50° C. during the method of making the quaternary onium aromatic sulfonate.

4 . The method of claim 1 , wherein the acidic medium is selected from the group consisting of strong mineral acids and strongly acidic type ion exchange resins.

5 . The method of claim 1 , wherein the quaternary compound is represented by formula:

Y—X(R 4 ) 4

wherein X is phosphorus; each R 4 independently comprises aliphatic or aromatic, substituted or unsubstituted, carbocyclic or heterocyclic radicals; and Y comprises hydroxide, OCOR 5 , and OR 5 , and wherein R 5 comprises aliphatic and aromatic, substituted or unsubstituted radicals.

6 . The method of claim 1 , wherein the quaternary compound comprises tetra-n-butylphosphonium hydroxide.

7 . The method of claim 1 , further comprising adjusting a pH of the first solution to about 4 to about 6.

8 . The method of claim 1 , wherein the solvent for said aromatic sulfonic acid salt comprises water, C 1 -C 4 aliphatic alcohols, tetrahydrofliran, acetonitrile, C 7 -C 9 aromatic hydrocarbons, or combinations containing at least one of these solvents.

9 . The method of claim 1 , wherein said organic solvent for extraction comprises halogenated aliphatic and aromatic compounds, aliphatic and aromatic hydrocarbons, cyclic and acylic ethers, and combinations containing at least one of these solvents.

10 . A method of making a quaternary onium aromatic sulfonate comprising:

preparing in a solvent a first solution comprising an aromatic sulfonic acid salt having the formula:

wherein “T” is an alkali metal, “a” has a value of 1 or 2, and “b” has a value of 0 ; G 1 is an aromatic group; each Y 1 independently comprises hydrogen, a monovalent hydrocarbon group, halogen, or “OR”, “R” is a monovalent hydrocarbon group; “s” and “u” each represents an integer equal to zero, “q” represents any integer from and including zero through the number of positions on G 1 available for substitution, “t” represents an integer equal to one;

contacting the first solution with an acidic medium to convert the alkali metal aromatic sulfonic acid salt to an aromatic sulfonic acid;

mixing the aromatic sulfonic acid with a quaternary compound;

extracting the mixture with an organic solvent to provide a second solution; and

evaporating the organic solvent from the second solution to obtain the quaternary onium aromatic sulfonate represented by the formula:

wherein each R 1 independently comprises aliphatic or aromatic, substituted or unsubstituted, carbocyclic or heterocyclic radicals, each “X” is selected from the group consisting of phosphorus and nitrogen; “a” has a value of 1 or 2 and “b” has a value of zero; G 1 is an aromatic group; each Y 1 independently comprises hydrogen, a monovalent hydrocarbon group, alkenyl, allyl, halogen, bromine, chlorine; nitro; or OR, wherein “R” is a monovalent hydrocarbon group; “t” represents an integer equal to one; “s” and “u” each represents an integer equal to zero, and “q” represents any integer from and including zero through the number of positions on G 1 available for substitution.

11 . The method of claim 10 , wherein said alkali metal is selected from the group consisting of lithium, sodium, potassium, rubidium, and cesium.

12 . The method of claim 10 , further comprising maintaining a temperature of about 10° C. to about 50° C. during the preparation.

13 . The method of claim 10 , wherein the quaternary compound comprises the formula X(R 4 ) 4 —Y, wherein X is selected from the group consisting of phosphorus and nitrogen; each R 4 independently comprises aliphatic or aromatic, substituted or unsubstituted, carbocyclic or heterocyclic radicals; and Y comprises hydroxide, OCOR 5 , and OR 5 , wherein R 5 independently comprises aliphatic and aromatic, substituted or unsubstituted radicals.

14 . The method of claim 10 , wherein the acid medium is an ion exchange resin bearing sulfonic acid groups.

15 . The method of claim 10 , wherein the quaternary compound is tetra-n-butylphosphonium hydroxide.

16 . The method of claim 10 , further comprising adjusting a pH of the first solution to about 4 to about 6.

17 . The method of claim 10 , wherein the solvent for said aromatic sulfonic salt comprises water, C 1 -C 4 aliphatic alcohols, tetrahydrofuran, acetonitrile, C 7 -C 9 aromatic hydrocarbons, and mixtures thereof.

18 . The method of claim 10 , wherein said organic solvent for extraction comprises halogenated aliphatic and aromatic compounds, aliphatic and aromatic hydrocarbons, cyclic and acylic ethers, and mixtures thereof.

19 . A method of making a polyorganosiloxane-functionalized aromatic sulfonate comprising:

forming a reaction mixture comprising:

a hydroxyalkyl- or a hydroxyaryl-terminated polydimethylsiloxane represented by the formula:

wherein “Z” is selected from the group consisting of (CH 2 ) m′ , wherein “m′” has a value from about 2 to about 10, and divalent substituted and unsubstituted aromatic radicals; and n′ has a value of about 5 to about 20;

a quaternary sulfonate salt of an aromatic sulfocarboxylic acid having the formula:

wherein each R 1 is independently selected from aliphatic or aromatic, substituted or unsubstituted, carbocyclic or heterocyclic radicals, and X is selected from the group consisting of phosphorus and nitrogen;

a catalyst composition, and

a solvent;

stirring the reaction mixture; and

heating the reaction mixture to a temperature and time effective to produce the polyorganosiloxane-functionalized aromatic sulfonate having the formula:

wherein each R 1 independently selected from aliphatic or aromatic, substituted or unsubstituted, carbocyclic or heterocyclic radicals, and X is selected from the group consisting of phosphorus and nitrogen; “Z” is selected from the group consisting of (CH 2 ) m′ , wherein M′ has a value from about 2 to about 10, and divalent substituted and unsubstituted aromatic radicals; and n′ has a value of about 5 to about 20.

20 . The method of claim 19 , wherein R 1 comprises an n-butyl group.

21 . The method of claim 19 , wherein the catalyst composition is selected from the group consisting of a carbodiimide compound of the formula:

R 6 —N═C═N—R 6 ,

wherein R 6 is independently selected from monovalent alkyl and aryl, substituted and unsubstituted radicals; 1-hydroxybenzotriazole, tertiary amines of the formula (R 7 ) 3 N, wherein R 7 is independently selected from C 1 -C 8 linear and branched alkyl groups; and a heterocyclic nitrogen base.

22 . The method of claim 21 , wherein the carbodiimide compound is selected from the group consisting of 1,3-dicyclohexylcarbodiimide, 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride, 1,3-diisopropylcarbodiimide, and mixtures thereof.

23 . The method of claim 21 , wherein the heterocyclic nitrogen base is selected from the group consisting of substituted and unsubstituted pyridine, imidazoles, pyrrolidines, and mixtures thereof.

24 . The method of claim 19 , wherein the solvent comprises C 1 -C 4 aliphatic nitriles, dichloromethane, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, and chlorotoluenes.

25 . The method of claim 19 , further comprising heating the reaction mixture to a temperature of about 50° C. to about a refluxing temperature of the reaction mixture for about 8 to about 30 hours.

26 . A method of making a benzene-1-methoxy-3-(n-pentadecyl)-4,6-ditetrabutylphosphoniumsulfonate compound comprising:

contacting an aqueous solution of an alkali metal salt of a benzene-1-methoxy-3-n-pentadecyl-4,6-disulfonic acid with a strongly acidic type ion exchange resin to generate a free acid of the alkali metal salt in the aqueous solution;

contacting the aqueous solution with tetra-n-butylphosphonium hydroxide in an amount effective to lower a pH of the solution to about 5 to about 6;

mixing the aqueous solution with an organic solvent;

separating the organic solvent from the aqueous solution; and

evaporating the organic solvent to obtain the benzene-1-methoxy-3-(n-pentadecyl)-4,6-ditetrabutylphosphoniumsulfonate compound.

27 . A method of making an alkylated diphenyloxide tetrabutylphosphoniumsulfonate compound having the formula:

wherein a′ has a value of zero or one, R 2 can occupy an ortho or a para position on the aromatic ring, and is independently selected from the group consisting of C 6 to C 20 linear and branched alkyl groups; said method comprising:

contacting an aqueous solution with an acidic type ion exchange resin, wherein the aqueous solution comprises a compound represented by the formula:

wherein a′ has a value of zero or one, T is selected from hydrogen and sodium;

contacting the aqueous solution with tetra-n-butylphosphonium hydroxide in an amount effective to adjust a pH of the aqueous solution to about 5 to about 5.5;

mixing the aqueous solution with an organic solvent;

separating the organic solvent from the aqueous solution; and

evaporating the solvent from the solution to obtain the alkylated diphenyloxide tetrabutylphosphoniumsulfonate compound.

28 . A method of making a bis(tetrabutylphosphonium) polyorganosiloxane-functionalized aromatic sulfonate compound having the formula:

wherein n″ is an integer having a value of about 7; said method comprising:

forming a reaction mixture comprising:

a hydroxyalkyl-terminated polydimethylsiloxane having the formula:

wherein n″ is an integer with a value of about 7;

a quaternary sulfonate salt of an aromatic sulfocarboxylic acid having the formula,

a catalyst composition comprising 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, and triethylamine;

a solvent; and

heating the reaction mixture to a temperature and for a time effective to produce the bis(tetrabutylphosphonium) polyorganosiloxane-functionalized aromatic sulfonate compound.

29 . The method of claim 28 , wherein the temperature is maintained from about 50° C. to the refluxing temperature of the reaction mixture.

30 . The method of claim 28 , wherein said solvent comprises C 1 -C 4 nitriles, dichloromethane, 1,2-dichloroethane, chlorobenzene, dichlorobenzene, and chlorotoluenes.

31 . A method of making an antistatic or antidust thermoplastic polymer molding composition comprising:

dry-blending an aromatic sulfonate compound with a thermoplastic resin to produce a molding composition, wherein the aromatic sulfonate compound is represented by the formula:

wherein each R 1 independently comprises aliphatic or aromatic, substituted or unsubstituted, carbocyclic or heterocyclic radicals, each X is selected from the group consisting of phosphorus and nitrogen; wherein “a” is 0, 1 or 2, and “b” is 0, 1 or 2 with the proviso that (a+b) is an integer greater than or equal to 1; G 1 is an aromatic group; E comprises a bis(carbonyloxyalkyl) polydiorganosiloxane, a bis(carbonyloxyaryl) polydiorganosiloxane, or an ether linkage; each Y 1 independently comprises hydrogen, a monovalent hydrocarbon group, alkenyl, allyl, halogen, bromine, chlorine; nitro; or OR, wherein R is a monovalent hydrocarbon group; “q” represents any integer from and including zero through the number of positions on G 1 available for substitution; “t” represents an integer equal to at least one; “s” represents an integer equal to either zero or one; and “u” represents any integer including zero; with the proviso that when E is an ether linkage, then X is phosphorus.

32 . A method of making an antistatic or antidust thermoplastic polymer molding composition comprising:

combining an aromatic sulfonate compound with a thermoplastic resin melt processing equipment, wherein the aromatic sulfonate compound is represented by the formula:

wherein each R 1 independently comprises aliphatic or aromatic, substituted or unsubstituted, carbocyclic or heterocyclic radicals, each X is selected from the group consisting of phosphorus and nitrogen; wherein “a” is 0, 1 or 2, and “b” is 0, 1 or 2 with the proviso that (a+b) is an integer greater than or equal to 1; G 1 is an aromatic group; E comprises a bis(carbonyloxyalkyl) polydiorganosiloxane, a bis(carbonyloxyaryl) polydiorganosiloxane, or an ether linkage; each Y 1 independently comprises hydrogen, a monovalent hydrocarbon group, alkenyl, allyl, halogen, bromine, chlorine; nitro; or OR, wherein R is a monovalent hydrocarbon group; “q” represents any integer from and including zero through the number of positions on G 1 available for substitution; “t” represents an integer equal to at least one; “s” represents an integer equal to either zero or one; and “u” represents any integer including zero; with the proviso that when E is an ether linkage, then X is phosphorus.