Antistatic agents and polymer compositions derived therefrom
View Patent ↗An antistatic additive comprises a quaternary onium organosilicon compound having the formula (I) wherein each R 1 independently comprises an aliphatic or aromatic functional groups that may be substituted or unsubstituted; X comprises phosphorus or nitrogen; each R 2 independently comprises an aliphatic or aromatic functional group that may be substituted or unsubstituted; each R 3 independently comprises a hydrogen or an aliphatic or aromatic functional group that may be substituted or unsubstituted; and “n” has a value of about 1 to about 20.
1. A quaternary onium organosilicon compound having the formula (I):
wherein each R 1 independently comprises an aliphatic or aromatic functional group; X is phosphorus; each R 2 independently comprises an aliphatic or aromatic functional group; each R 3 independently comprises an aliphatic functional group, an aromatic functional group, or a hydrogen; and “n” has a value of 1 to about 20.
2. The compound of claim 1 , wherein each R 1 is an n-butyl radical, X is phosphorus, each R 2 is a methyl radical, each R 3 is a hydrogen, and “n” has a value of 2 to about 10.
3. The compound of claim 1 , wherein each R 1 is an n-butyl radical, X is phosphorus, each R 2 is a methyl radical, each R 3 is a hydrogen, and “n” has a value of 3.
4. A polymer composition comprising a polymer and a quaternary onium organosilicon compound having the formula (I):
wherein each R 1 independently comprises an aliphatic or aromatic functional group; X comprises phosphorus or nitrogen; each R 2 independently comprises an aliphatic or aromatic functional group; each R 3 independently comprises an aliphatic functional group, an aromatic functional group, or a hydrogen; and “n” has a value of 1 to about 20.
5. The composition of claim 4 , wherein the organosilicon compound is present in an amount of about 2.5×10 −3 parts to about 6 parts per 100 parts of the polymer.
6. The composition of claim 4 , wherein the organosilicon compound is present in an amount of about 3×10 −2 parts to about 6 parts per 100 parts of the polymer.
7. The composition of claim 4 , wherein the organosilicon compound is present in an amount of about 0.3 parts to about 6 parts per 100 parts of the polymer.
8. The composition of claim 4 , wherein the polymer comprises at least one condensation or addition polymer.
9. The composition of claim 8 , wherein said polymer comprises at least one aromatic polycarbonate, polyestercarbonate, polyphenylene sulfide, polyetherimide, polyester, polyphenylene ether, polyphenylene ether/styrene polymer blends, polyamide, polyketone, acrylonitrile-butadiene-styrene copolymer, styrene-acrylonitrile copolymer, polyolefin, blends thereof, or blends thereof with other materials.
10. The composition of claim 9 , wherein the polycarbonate and polyestercarbonate are obtained from polymerization processes comprising melt transesterification, interfacial polymerization, solid state polymerization, solution, redistribution processes, or combinations thereof.
11. The composition of claim 10 , wherein the organosilicon compound comprises
or a mixture thereof.
12. An antistatic article comprising the polymer composition of claim 11 .
13. The article of claim 12 , wherein the article comprises forward lighting assemblies, automotive headlamp lenses, fog lamp lenses, ophthalmic devices, conveyor belt systems, printer devices, and display panel devices for appliances.
14. A method of making a quaternary onium organosilicon compound comprising:
contacting a solution comprising a first solvent and an organosilicon monosulfonic acid salt having the formula
wherein M is an alkali metal, each R 2 independently comprises an aliphatic or aromatic functional group; each R 3 independently comprises an aliphatic functional group, an aromatic functional group, or a hydrogen; and n is an integer having a value of 1 to about 20; with an acidic medium to generate the corresponding free sulfonic acid composition,
contacting the free sulfonic acid composition with a quaternary phosphorus compound to form a neutralization mixture,
extracting the neutralization mixture with a second solvent to provide an extractant; and
evaporating substantially all the solvent from the extractant to isolate a quaternary onium organosilicon compound having the formula (I):
wherein each R 1 independently comprises an aliphatic or aromatic functional group; X is phosphorus; each R 2 independently comprises an aliphatic or aromatic functional group; each R 3 independently comprises an aliphatic functional group, an aromatic functional group, or a hydrogen; and “n” has a value of 1 to about 20.
15. The method of claim 14 , wherein the alkali metal comprises lithium, sodium, potassium, rubidium, or cesium.
16. The method of claim 14 , wherein the free sulfonic acid composition is contacted with the quaternary compound at a temperature of about 10° C. to about 50° C.
17. The method of claim 14 , wherein the free sulfonic acid composition is contacted with the quaternary compound at a temperature of about 20° C. to about 30° C.
18. The method of claim 14 , wherein the acidic medium comprises a strong mineral acid, a polymeric acidic ion exchange resins or a combination thereof.
19. The method of claim 18 , wherein the acid medium is a polymeric acidic ion exchange resin bearing sulfonic acid groups.
20. The method of claim 14 , wherein the quaternary phosphorus compound comprises P(R 1 ) 4 —Y, wherein; each R 1 independently comprises an aliphatic or aromatic functional group; and Y comprises hydroxide, OCOR 4 , and OR 4 , wherein R 4 comprises a substituted or unsubstituted, aliphatic or aromatic functional group.
21. The method of claim 20 , wherein R 1 is n-butyl, and Y is hydroxide.
22. The method of claim 20 , wherein the quaternary compound comprises tetraethylphosphonium hydroxide, tetra-n-butylphosphonium hydroxide, tetra-n-octylphosphonium hydroxide, or tetraphenylphosphonium hydroxide.
23. Tho method of claim 14 , wherein the pH of the neutralization mixture is about 4 to about 6.
24. The method of claim 14 , wherein the pH of the neutralization mixture is about 5 to about 5.5.
25. The method of claim 14 , wherein the first solvent comprises water, C 1 -C 4 aliphatic alcohols, tetrahydrofuran, acetonitrile, C 7 -C 9 aromatic hydrocarbons, or mixtures thereof.
26. The method of claim 16 , wherein the quaternary onium organosilicon compound is tetra-n-butylphosphonium 3-trimethylsilylpropanesulfonate.
27. A method of making tetra-n-butylphosphonium 3-trimethylsilylpropanesulfonate comprising:
contacting a solution comprising a first solvent and sodium 3-trimethylsilylpropanesulfonate with an acidic ion exchange resin to generate a solution of free 3-trimethylsilylpropanesulfonic acid;
contacting the solution of free 3-trimethylsilylpropanesulfonic acid with tetra-n-butylphosphonium hydroxide to form a mixture having a pH of about 5.0 to about 5.5;
extracting the mixture with a second solvent to form an extractant comprising tetra-n-butylphosphonium 3-trimethylsilylpropanesulfonate; and
evaporating substantially all of the solvent from the extractant to isolate tetra-n-butylphosphonium 3-trimethylsilylpropanesulfonate.
28. The method of claim 27 , wherein said first solvent comprises water, C 1 -C 4 aliphatic alcohols, tetrahydrofuran, acetonitrile, C 7 -C 9 aromatic hydrocarbons, or mixtures thereof.
29. The method of claim 27 , wherein the second solvent comprises halogenated aliphatic and aromatic compounds, aliphatic and aromatic hydrocarbons, cyclic and acylic ethers, or mixtures thereof.
30. A method of making an antistatic thermoplastic polymer composition comprising:
combining a quaternary onium organosilicon compound with a thermoplastic resin in melt, wherein the organosilicon compound is represented by the formula:
wherein each R 1 independently comprises an aliphatic or aromatic functional group; X comprises phosphorus or nitrogen; each R 2 independently comprises an aliphatic or aromatic functional group; each R 3 independently comprises an aliphatic functional group, aromatic functional group, or a hydrogen; and “n” has a value of 1 to about 20.
31. A method of making an antistatic thermoplastic polymer composition comprising:
dry-blending a thermoplastic polymer with a quaternary onium organosilicon compound, wherein the organosilicon compound is represented by the formula:
wherein each R 1 independently comprises an aliphatic or aromatic functional group; X comprises phosphorus or nitrogen; each R 2 independently comprises an aliphatic or aromatic functional group; each R 3 independently comprises an aliphatic functional group, aromatic functional group, or a hydrogen; and “n” has a value of 1 to about 20.