S-(Alpha, Alpha'-Disubstituted-Alpha"-Acetic Acid) Substituted Dithiocarbonate Derivatives for Controlled Radical Polymerizations, Process and Polymers Made Therefrom
AssigneeLubrizol Advanced Materials, Inc.
InventorJohn Lai
Life of this patent
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Abstract
Dithiocarbonate derivatives are disclosed, along with a process for preparing the same. The dithiocarbonate compounds can be utilized as initators, chain transfer agents and/or terminators in controlled free radical polymerizations. The dithiocarbonates can be used to produce polymers having narrow molecular weight distribution. Advantageously, the compounds of the present invention can also introduce functional groups into the resulting polymers. The dithiocarbonate compounds have low odor and are substantially colorless.
Claims13
1-52. (canceled)
A method for forming a O-alkyl-S-(α,α′-disubstituted-α″ acetic acid) xanthate compound, comprising the steps of:
- reacting a alkoxylate salt of a xanthate compound, carbon disulfide, a haloform, and a ketone in the presence of a base, and optionally a solvent and a catalyst, to form a reaction product;
- and
- acidifying said reaction product to form said O-alkyl-S-(α,α′-disubstituted-α″ acetic acid) xanthate compound.
A method for forming an O-alkyl-S-(α,α′-disubstituted-α″ acetic acid) xanthate polymer or copolymer, comprising the steps of:
- providing a O-alkyl-S-(α,α′-disubstituted-α″-acetic acid) xanthate compound having the formula:
- wherein R12 and R13, independently, can be the same or different, can be a linear or branched alkyl having from 1 to about 12 carbon atoms;
- or an aryl group having from 6 to about 18 carbon atoms, optionally containing heteroatoms;
- or R12 and R13 can form or be a part of a substituted or unsubstituted cyclic ring having from 3 to about 12 carbon atoms;
- wherein R14 is optionally substituted, and can be a linear or branched allyl having from 1 to about 12 carbon atoms, an aryl group optionally saturated or unsaturated;
- an arylalkyl having from about 7 to about 18 carbon atoms;
- an acyl group;
- an alkene group;
- an alkenealkyl having from 3 to about 18 carbon atoms;
- an alkylene group;
- an alkoxyalkyl;
- derived from a polyalkylene glycol;
- derived from a polyalkylene glycol monoalkyl ether having from about 3 to about 200 carbon atoms;
- derived from a polyalkylene glycol monoaryl ether having from about 3 to about 200 carbon atoms, a polyfluoroalkyl;
- a phosphorous containing alkyl;
- or a substituted or unsubstituted aryl ring containing heteroatoms;
- wherein said “j” is 1 to about 4;
- and
- reacting at least one vinyl-containing monomer, or at least one conjugated diene monomer with said O-alkyl-S-(α,α′-disubstituted-α″-acetic acid) xanthate compound.
Dependencies are inferred from the claim text.