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US 2003/0120101 A1Published application
S-(alpha, alpha'-disubstituted-alpha' '-acetic acid) substituted dithiocarbonate derivatives for controlled radical polymerizations, process and polymers made therefrom
AssigneeNoveon, Inc.
InventorJohn Ta-Yuan Lai
Life of this patent
Estimating the term…
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.
Claims64
A composition, comprising:
- a dithiocarbamate compound having the formula:
- 69
- wherein R15 and R16, independently, can be the same or different, can optionally contain heteroatoms, optionally can be substituted, and can be hydrogen;
- a linear or branched alkyl having from 1 to about 18 carbon atoms;
- an aryl group having from 6 to about 18 carbon atoms, optionally saturated or unsaturated;
- an arylalkyl having from 7 to about 18 carbon atoms;
- an alkenealkyl having from 3 to about 18 carbon atoms;
- derived from polyalkylene glycol ether;
- or is derived from an amine;
- or R15 and R16 can also form a substituted or unsubstituted cyclic ring with the nitrogen and having a total of 4 to about 12 carbon atoms;
- wherein R12 and R13, independently, can be the same or different, can optionally be substituted, and 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 and be part of a substituted or unsubstituted cyclic ring having from 3 to about 12 carbon atoms;
- and
- wherein j is from 1 to about 4.
12 more elements
A composition, comprising:
- a dithiocarbamate polymer or copolymer having the formula:
- 70
- wherein R15 and R16, independently, can be the same or different, can optionally contain heteroatoms, optionally can be substituted, and can be hydrogen;
- a linear or branched alkyl having from 1 to about 18 carbon atoms;
- an aryl group having from 6 to about 18 carbon atoms, optionally saturated or unsaturated;
- an arylalkyl having from 7 to about 18 carbon atoms;
- an alkenealkyl having from 3 to about 18 carbon atoms;
- derived from polyalkylene glycol ether;
- or is derived from an amine;
- or R15 and R16 can also form a substituted or unsubstituted cyclic ring with the nitrogen and having a total of 4 to about 12 carbon atoms;
- wherein R12 and R13, independently, can be the same or different, can optionally be substituted, and 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 and be part of a substituted or unsubstituted cyclic ring having from 3 to about 12 carbon atoms;
- wherein j is from 1 to about 4;
- wherein said polymer is derived from at least one conjugated diene monomer, a vinyl containing monomer, or combinations thereof, with the proviso that each repeat unit can be the same or different;
- and
- wherein f is from 1 to about 10,000.
14 more elements
A composition, comprising:
- an alkoxy dithiocarbonate compound having the formula:
- 72
- 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 alkyl 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;
- and
- wherein said “a” is 1 to about 4.
16 more elements
A composition, comprising:
- a polymer or copolymer derived from a xanthate compound having the formula:
- 73
- 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 alkyl 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 the polymer is derived from at least one conjugated diene monomer, or a vinyl containing monomer or combinations thereof, with the proviso that each polymer repeat unit can be the same or different;
- wherein said g is from about 1 to about 10,000;
- and
- wherein said “a” is 1 to about 4.
18 more elements
A method for forming a S-(α,α′-disubstituted-α″-acetic acid) dithiocarbamate compound, comprising the steps of:
- reacting a metal salt of a dithiocarbamate, 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 S-(α,α′-disubstituted-α″-acetic acid) dithiocarbamate compound.
A method for forming a S-(α,α′-disubstituted-α″-acetic acid) dithiocarbamate polymer or copolymer, comprising the steps of:
- providing a S-(α,α′-disubstituted-α″-acetic acid) dithiocarbamate compound having the formula:
- 77
- wherein R15 and R16, independently, can be the same or different, can optionally contain heteroatoms, optionally can be substituted, and can be hydrogen;
- a linear or branched alkyl having from 1 to about 18 carbon atoms;
- an aryl group having from 6 to about 18 carbon atoms, optionally saturated or unsaturated;
- an arylalkyl having from 7 to about 18 carbon atoms;
- an alkenealkyl having from 3 to about 18 carbon atoms;
- derived from polyalkylene glycol ether;
- or is derived from an amine;
- or R15 and R16 can also form a substituted or unsubstituted cyclic ring, with the nitrogen and having a total of 4 to about 12 carbon atoms;
- wherein R12 and R3, independently, can be the same or different, can optionally be substituted, and 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 and be part of a substituted or unsubstituted cyclic ring having from 3 to about 12 carbon atoms;
- wherein j is from 1 to about 4;
- and
- reacting at least one vinyl-containing monomer, or at least one conjugated diene monomer with said S-(α,α′-disubstituted-α″-acetic acid) dithiocarbamate compound.
13 more elements
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:
- 81
- 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 alkyl 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.
17 more elements
Dependencies are inferred from the claim text.