Arylsulfinate salts in photoinitiator systems for polymerization reactions
원문보기
IPC분류정보
국가/구분
United States(US) Patent
등록
국제특허분류(IPC7판)
C08F-002/46
C08F-002/50
G03C-001/72
출원번호
UP-0380028
(2006-04-25)
등록번호
US-7541389
(2009-07-01)
발명자
/ 주소
Kalgutkar, Rajdeep S.
Palazzotto, Michael C.
출원인 / 주소
3M Innovative Properties Company
대리인 / 주소
Lown, Jean A.
인용정보
피인용 횟수 :
0인용 특허 :
70
초록▼
Compositions are provided that include an electron donor and a sensitizing compound. More specifically, the electron donor is an arylsulfinate salt. Methods of polymerization are also provided that can be used to prepare polymeric material from a photopolymerizable composition that includes ethyleni
Compositions are provided that include an electron donor and a sensitizing compound. More specifically, the electron donor is an arylsulfinate salt. Methods of polymerization are also provided that can be used to prepare polymeric material from a photopolymerizable composition that includes ethylenically unsaturated monomers and a photoinitiator system. The photoinitiator system includes an electron donor and a sensitizing compound.
대표청구항▼
We claim: 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 ab
We claim: 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 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. 2. The method of claim 1, wherein the anion of the arylsulfinate salt is benzenesulfinate substituted with an electron withdrawing group electron selected from halo, cyano, fluoroalkyl, perfluoroalkyl, carboxy, alkoxycarbonyl, aryloxycarbonyl, halocarbonyl, formyl, carbonyl, sulfo, alkoxysulfonyl, aryloxysulfonyl, perfluoroalkylsulfonyl, alkylsulfonyl, azo, alkenyl, alkynyl, dialkylphosphonato, diarylphosphonato, aminocarbonyl, or combinations thereof and the cation is a tetraalkylammonium ion. 3. The method of claim 1, wherein the anion of the arylsulfinate salt is 4-chlorobenzenesulfinate, 4-cyanobenzenesulfinate, 4-ethoxycarbonylbenzenesulfinate, 4-trifluoromethylbenzenesulfinate, 3-trifluoromethylbenzenesulfinate, 1-anthraquinone sulfinate, 1-naphthalenesulfinate, or 2-naphthalenesulfinate. 4. The method of claim 1, wherein the Ar1 group of the arylsulfinate salt is anthryl, naphthyl, acenaphthyl, phenanthryl, phenanthrenyl, perylenyl, anthracenyl, anthraquinonyl, anthronyl, biphenyl, terphenyl, 9,10-dihydroanthracenyl, or fluorenyl, said Ar1 group being unsubstituted or substituted with an electron withdrawing group or electron withdrawing group in combination with an electron donating group. 5. The method of claim 1, wherein the Ar1 group of the arylsulfinate salt is quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, cinnolinyl, benzofuranyl, benzomercaptophenyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, indolyl, phthalazinyl, benzothiadiazolyl, benzotriazinyl, phenazinyl, phenanthridinyl, acridinyl, or indazolyl, said Ar1 group being unsubstituted or substituted with an electron withdrawing group or an electron withdrawing group in combination with an electron donating group. 6. The method of claim 1, wherein the Ar1 group of the arylsulfinate salt is a substituted phenyl, an unsubstituted or substituted naphthyl, or an unsubstituted or substituted anthraquinonyl, said substituted Ar1 having a substituent that is an electron withdrawing group or an electron withdrawing group in combination with an electron donating group. 7. The method of claim 1, wherein the photopolymerizable composition comprises 0.1 to 4 wt % electron donor and 5 ppm to 4 wt % sensitizing compound based on the weight of the monomer. 8. The method of claim 1, wherein the ethylenically unsaturated monomer comprises a monoacrylate, monomethacrylate, diacrylate, dimethacrylate, polyacrylate, polymethacrylate, or combinations thereof.
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