US4201640A
Expired / Lapsed
US
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Method for producing bis-[4-(diphenylsulfonio)phenyl] sulfide bis-M.X6
Assignee: Primerica Inc
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Filing: 1979-03-14
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Granted: 1980-05-06
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Expires: 1999-03-14
Abstract
Abstract A highly effective photoinitiator for cationic polymerization of monomer formulations is prepared by reacting bis-[4-(diphenylsulfonio)phenyl] sulfide bis-halide wherein halide is chloride or bromide in an aqueous solution with a compound having the formula T.MF6 wherein M is one of phosphorus, antimony or arsenic and T is hydrogen or a metal whose halide salt is water soluble. The two compounds react in the aqueous medium to produce a precipitate which includes at least about 50 percent by weight bis-[4-(diphenylsulfonio) phenyl] sulfide bis-MF6, and this precipitate may be recovered and dried for utilization without further purification if so desired. Purification may be effected by dissolving the dried product in an organic solvent, cooling the solvent to precipitate the impurities, and thereafter recovering relatively pure bis-[4-(diphenylsulfonio) phenyl] sulfide bis-MF6 by chilling the solvent solution to form a precipitate, and then separating and drying the precipitate. The preferred compounds are those wherein the substituent M is phosphorus so that the product comprises bis-[4-(diphenylsulfonio) phenyl] sulfide bis-hexafluorophosphate. The cationic polymerization processes utilize the photoinitiator in an amount equal to about 0.5-6.0 percent by weight of the monomer therein.
Inventors
- 👤 William R. Watt
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 12:34
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; C; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G65/00; C08G65/02; C08G65/04; C08G65/06; C08G65/08; C08G65/10; C08G85/00
Claims Analysis
Total Claims: 9
Claim 1
Independent Claim
187 words
In a method of polymerization of a cationically polymerizable monomer, the steps comprising: A. making a photoinitiator by: (1) providing a first reactant comprising bis-[4-(diphenylsulfonio)phenyl] sulfide bis-halide wherein halide is chloride or bromide; (2) admixing said first reactant in an aqueous solution with a second reactant having the formula T.MF 6 wherein M is one of phosphorus, antimony or arsenic, T is hydrogen or a metal whose halide salt is water soluble, said reactants reacting to produce a precipitate including bis-[4-(diphenylsulfonio) phenyl] sulfide bis-MF 6 ; (3) recovering said precipitate; and (4) drying said precipitate at a temperature below about 50° C. for at least an initial period to dewater said precipitate and recover a frangible product containing at least 50 percent by weight bis-[4-(diphenylsulfonio) phenyl] sulfide bis-MF 6 based upon solids, said product comprising a photoinitiator; B. admixing said photoinitiator with a cationically polymerizable monomer formulation in an amount equal to 0.5-6.0 percent by weight of the monomer therein; and C. exposing said admixture to a source of electromagnetic radiation to decompose said photoinitiator and produce a Lewis acid to initiate polymerization of said polymerizable monomer.
Claim 2
Dependent Claim
187 words
In a method of polymerization of a cationically polymerizable monomer, the steps comprising: A. making a photoinitiator by: (1) providing a first reactant comprising bis-[4-(diphenylsulfonio)phenyl] sulfide bis-halide wherein halide is chloride or bromide; (2) admixing said first reactant in an aqueous solution with a second reactant having the formula T.MF 6 wherein M is one of phosphorus, antimony or arsenic, T is hydrogen or a metal whose halide salt is water soluble, said reactants reacting to produce a precipitate including bis-[4-(diphenylsulfonio) phenyl] sulfide bis-MF 6 ; (3) recovering said precipitate; and (4) drying said precipitate at a temperature below about 50° C. for at least an initial period to dewater said precipitate and recover a frangible product containing at least 50 percent by weight bis-[4-(diphenylsulfonio) phenyl] sulfide bis-MF 6 based upon solids, said product comprising a photoinitiator; B. admixing said photoinitiator with a cationically polymerizable monomer formulation in an amount equal to 0.5-6.0 percent by weight of the monomer therein; and C. exposing said admixture to a source of electromagnetic radiation to decompose said photoinitiator and produce a Lewis acid to initiate polymerization of said polymerizable monomer.
Claim 3
Dependent Claim
33 words
The method in accordance with claim 1 wherein said dewatered product is, subsequent to having reached a point where it is readily frangible, dried further at a temperature of up to 110° C.
Claim 4
Dependent Claim
16 words
The method in accordance with claim 1 wherein said halide of said first reactant is chloride.
Claim 5
Dependent Claim
127 words
The method in accordance with claim 1 wherein said dewatered product is purified in accordance with the following steps to provide the photoinitiator: (A) dissolving the dried precipitate in a solvent therefor selected from the group consisting of C 1 -C 3 alcohols, C 3 -C 6 ketones, and C 2 -C 6 esters, at an elevated temperature in excess of 50° C. but below the boiling point of said solvent; (B) cooling said solvent solution to form an insoluble precipitate; (C) separating said solution from said precipitate; (D) cooling the solution to a temperature below about 10° C. effective to precipitate out substantially pure product; (E) recovering the precipitate; and (F) drying the precipitate to produce a photoinitiator comprising substantially bis-[4-(diphenylsulfonio) phenyl] sulfide bis-MF 6 .
Claim 6
Dependent Claim
11 words
The method in accordance with claim 1 wherein M is phosphorus.
Claim 7
Dependent Claim
22 words
The method in accordance with claim 1 wherein said polymerizable formulation is an epoxidic prepolymer material polymerizable to a higher molecular weight.
Claim 8
Dependent Claim
30 words
The method in accordance with claim 6 wherein said epoxidic prepolymer material contains at least about 15 percent by weight of epoxidic prepolymer material having two epoxycycloalkyl groups per molecule.
Claim 9
Dependent Claim
48 words
The method in accordance with claim 6 wherein, following said exposure to electromagnetic radiation, said polymerizable formulation is maintained at a temperature of about 50°-90° C. for a period of at least about 0.5 second and less than about two minutes following initiation of said exposure to radiation.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1983-05-06 | 1983-11-05 | 1984-05-06 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-05-06 | 1987-11-05 | 1988-05-06 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-05-06 | 1991-11-05 | 1992-05-06 | $7700.00 | Window Closed / Lapsed |