Arylsulfinate salts in initiator systems for polymeric reactions
Assignee3M Innovative Properties Company
InventorsRajdeep S. Kalgutkar, Michael C. Palazzotto
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Abstract
Compositions are provided that that can be used as an initiator system for free radical polymerization reactions. More specifically, the initiator systems include an electron acceptor and an electron donor. The electron donors are arylsulfinate salts having a cation that contains at least one carbon atom and either a positively charged nitrogen atom or a positively charged phosphorus atom. Methods of polymerization are also provided that can be used to prepare polymeric material with the initiator systems. The initiator systems can be thermal initiator systems, photoinitiator systems, or combinations thereof.
Claims23
A composition comprising:
- an electron donor comprising an arylsulfinate salt having a anion of Formula I
- Ar1—SO2− I
- and a cation having at least one carbon atom and either a positively charged nitrogen atom or a positively charged phosphorus atom, said electron donor having an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, wherein
- Ar1 is a substituted phenyl, an unsubstituted or substituted C7-30 aryl, or an unsubstituted or substituted C3-30 heteroaryl, said substituted Ar1 having a substituent that is an electron withdrawing group or an electron withdrawing group in combination with an electron donating group;
- the cation is selected from
- 1) a phosphorous-containing cation of Formula III
- where each R2 is independently an unsubstituted alkyl, an alkyl substituted with a hydroxy, an unsubstituted aryl, or an aryl substituted wit an alkyl, hydroxy, or combinations thereof;
- or
- 2) a nitrogen-containing cation having a ring structure comprising a 4 to 12 member heterocyclic group having a positively charged nitrogen atom, said heterocyclic being saturated or unsaturated and having up to 3 heteroatoms selected from oxygen, sulfur, nitrogen, or combinations thereof, wherein said ring structure is unsubstituted or substituted with a substituent selected from an alkyl, aryl, acyl, alkoxy, aryloxy, halo, mercapto, amino, hydroxy, azo, cyano, carboxy, alkoxycarbonyl, aryloxycarbonyl, halocarbonyl, or combinations thereof;
- and
- an electron acceptor having a reduction potential in N,N-dimethylformamide of +0.4 to −1.0 volts versus a silver/silver nitrate reference electrode.
Dependencies are inferred from the claim text.