US 7,541,389 B2
Arylsulfinate salts in photoinitiator systems for polymerization reactions
Rajdeep S. Kalgutkar, St. Paul, Minn. (US); and Michael C. Palazzotto, Woodbury, Minn. (US)
Assigned to 3M Innovative Properties Company, St. Paul, Minn. (US)
Filed on Apr. 25, 2006, as Appl. No. 11/380,028.
Application 11/380028 is a division of application No. 10/847523, filed on May 17, 2004, granted, now 7,064,152.
Claims priority of provisional application 60/506396, filed on Sep. 26, 2003.
Prior Publication US 2007/0249749 A1, Oct. 25, 2007
This patent is subject to a terminal disclaimer.
Int. Cl. C08F 2/46 (2006.01); C08F 2/50 (2006.01); G03C 1/72 (2006.01)
U.S. Cl. 522—15  [522/27; 522/28; 522/17] 8 Claims
 
1. A method of photopolymerization comprising irradiating a photopolymerizable composition with actinic radiation until the polymerizable composition gels or hardens, said photopolymerizable composition comprising:
an ethylenically unsaturated monomer;
a sensitizing compound capable of absorbing a wavelength of actinic radiation in the range of 250 nanometers to 1000 nanometers, the sensitizing compound comprising a dye selected from a ketone, xanthene, acridine, thiazole, thiazine, oxazine, azine, aminoketone, aromatic polycyclic hydrocarbon, p-substituted aminostyryl ketone, aminotriaryl methane, cyanine, pyridinium, or triarylmethane;
an electron donor having an oxidation potential in N,N-dimethylformamide of 0.0 to +0.4 volts versus a silver/silver nitrate reference electrode, said electron donor comprising an arylsulfinate salt having an 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

OG Complex Work Unit Drawing
where each R2 is independently an unsubstituted alkyl, an alkyl substituted with a hydroxy, an unsubstituted aryl, or an aryl substituted with 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.