US4339567A
Expired / Lapsed
US
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Photopolymerization by means of sulphoxonium salts
Assignee: BASF Corp
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Filing: 1981-02-23
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Granted: 1982-07-13
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Expires: 2001-02-23
Abstract
Abstract Substances (I) capable of being converted into higher-molecular weight materials under the influence of a cationic catalyst, such as 1,2-epoxides, aminoplasts, vinyl monomers or prepolymers, or phenoplasts, are so converted by exposure to actinic radiation in the presence of a sulphoxonium salt (II) of formula ##STR1## where P denotes zero or 1, R 6 denotes an arylene or aralkylene group, R 7 denotes --H or a group of formula ##STR2## R 8 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, aryl, or aralkyl group, R 9 has the same meaning as R 8 but may alternatively represent a dialkylamino group or, if R 8 represents an alkyl group, R 9 may represent an arylamino group, R 10 and R 11 each independently have the same meaning as R 8 but may also each denote --H, r represents 1, 2, or 3, Z r- denotes an r-valent anion of a protic acid, and q denotes zero when p denotes zero, or zero or 1 when p denotes 1. Typical II are dimethylphenylsulphoxonium hexafluorophosphate and perchlorate, dimethylphenacylsulphoxonium hexafluorophosphate, and chloride, dodecylmethylbenzylsulphoxonium hexafluorophosphate, and 1,4-bis(1-oxo-2-(dimethylsulphoxonium)ethyl)benzene dihexafluoroarsenate. When I is a polyepoxide or a resol, it may be photopolymerized by means of II and subsequently crosslinked by heating with a latent heat-curing agent.
Inventors
- 👤 George E. Green
- 👤 Edward Irving
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-24 02:44
CPC Classifications
C; C08; C08G; C08G65/00; C08G65/02; C08G65/04; C08G65/06; C08G65/08; C08G65/10; C08G65/105; C08G59/00; C08G59/18; C08G59/68; C08K; C08K5/00; C08K5/36; C08K5/41; C08L; C08L61/00; C08L61/04; C08L61/06; G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; Y; Y10; Y10S; Y10S525/00; Y10S525/918; Y10T; Y10T428/00; Y10T428/31504; Y10T428/31511; Y10T428/31515; Y10T428/31518; Y10T428/31529
Claims Analysis
Total Claims: 11
Claim 1
Independent Claim
248 words
Compositions comprising (a) a compound, or mixture of compounds, capable of being transformed into a higher-molecular weight material under the influence of a cationic catalyst, (b) an effective amount of a sulfoxonium salt of the formula ##STR22## where p denotes zero or 1, R 6 denotes an arylene or aralkylene group of 4 to 25 carbon atoms linked directly through a carbon atom thereof to, if p denotes zero, the indicated sulfur atom or, if p denotes 1, to the indicated carbonyl carbon atom, R 7 denotes a hydrogen atom, or a group of formula ##STR23## R 8 denotes an alkyl group of 1 to 18 carbon atoms, an alkenyl group of 2 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a cycloalkylalkyl group of 4 to 8 carbon atoms, an aryl group of 4 to 24 carbon atoms, or an aralkyl group of 5 to 16 carbon atoms, R 9 has the same meaning as R 8 but may alternatively represent a dialkylamino group of 2 to 6 carbon atoms or, if R 8 denotes a said alkyl group, an arylamino group of 4 to 8 carbon atoms, R 10 and R 11 each independently have the same meaning as R 8 but may also each represent a hydrogen atom, r represents 1, 2, or 3, Z r- denotes an r-valent anion of a protic acid, and q denotes zero when p denotes zero, or zero or 1 when p denotes 1.
Claim 2
Dependent Claim
248 words
Compositions comprising (a) a compound, or mixture of compounds, capable of being transformed into a higher-molecular weight material under the influence of a cationic catalyst, (b) an effective amount of a sulfoxonium salt of the formula ##STR22## where p denotes zero or 1, R 6 denotes an arylene or aralkylene group of 4 to 25 carbon atoms linked directly through a carbon atom thereof to, if p denotes zero, the indicated sulfur atom or, if p denotes 1, to the indicated carbonyl carbon atom, R 7 denotes a hydrogen atom, or a group of formula ##STR23## R 8 denotes an alkyl group of 1 to 18 carbon atoms, an alkenyl group of 2 to 6 carbon atoms, a cycloalkyl group of 3 to 6 carbon atoms, a cycloalkylalkyl group of 4 to 8 carbon atoms, an aryl group of 4 to 24 carbon atoms, or an aralkyl group of 5 to 16 carbon atoms, R 9 has the same meaning as R 8 but may alternatively represent a dialkylamino group of 2 to 6 carbon atoms or, if R 8 denotes a said alkyl group, an arylamino group of 4 to 8 carbon atoms, R 10 and R 11 each independently have the same meaning as R 8 but may also each represent a hydrogen atom, r represents 1, 2, or 3, Z r- denotes an r-valent anion of a protic acid, and q denotes zero when p denotes zero, or zero or 1 when p denotes 1.
Claim 3
Dependent Claim
22 words
A composition according to claim 1, wherein R 6 denotes a homocyclic arylene or aralkylene group of 6 to 11 carbon atoms.
Claim 4
Dependent Claim
23 words
A composition according to claim 1, wherein R 8 and R 9 each denote an alkyl group of 1 to 12 carbon atoms.
Claim 5
Dependent Claim
74 words
A composition according to claim 1, wherein R 8 and R 9 each denote an alkyl group of 1 to 4 carbon atoms, or a phenyl or naphthyl group, which may be substituted in the ring or rings by one or two alkyl groups, each of 1 to 4 carbon atoms, by one or two alkoxy groups, each of 1 to 4 carbon atoms, or by one or two fluorine, chlorine, or bromine atoms.
Claim 6
Dependent Claim
85 words
A composition according to claim 1, where Z r- denotes Cl - , Br - , NO 3 - , HSO 4 - , ClO 4 - , H 2 PO 4 - , SO 4 -- , PO 4 --- , or an anion of formula MX.sub.n.sup.- IX where M denotes an atom of boron, bismuth, antimony, arsenic, or phosphorus, X denotes an atom of fluorine or chlorine, and n is 4, 5, or 6 and is one more than the valency of M.
Claim 7
Dependent Claim
38 words
A composition according to claim 1, wherein (b) is dimethylphenylsulfoxonium hexafluorophosphate, dimethylphenacylsulfoxonium hexafluorophosphate, dimethylphenacylsulfoxonium hexafluoroantimonate, diphenylphenacylsulfoxonium hexafluorophosphate, 1,4-bis(1-oxo-2-(dimethylsulfoxonium)ethyl)benzene dihexafluoroarsenate, (dimethylamino)diphenylsulfoxonium tetrafluoroborate, (diethylamino)diphenylsulfoxonium hexafluorophosphate, 1,4-bis(1-oxo-2-(dimethylsulfoxonium)ethyl)benzene dihexafluoroantimonate, dodecylmethylbenzylsulfoxonium hexafluorophosphate, triphenylsulfoxonium hexafluorophosphate, dimethylphenylsulfoxonium, perchlorate, dimethylphenacylsulfoxonium chloride, 1,4-bis(1-oxo-2-(dimethylsulfoxonium)ethyl)benzene dichloride, or tris(dimethylphenacylsulfoxonium) phosphate.
Claim 8
Dependent Claim
21 words
A composition according to claim 1, wherein (a) is a 1,2-epoxide, a vinyl monomer or prepolymer, an aminoplast, or a phenoplast.
Claim 9
Dependent Claim
23 words
A composition according to claim 7, wherein (a) is an epoxide resin, or a resol resin made from a phenol and an aldehyde.
Claim 10
Dependent Claim
22 words
A composition according to claim 1, containing 0.1 to 7.5 parts by weight of (b) per 100 parts by weight of (a).
Claim 11
Dependent Claim
26 words
A composition according to claim 8, which also contains a curing amount of a latent heat-curing agent for the epoxide resin or for the resol resin.
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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) | 1985-07-12 | 1986-01-11 | 1986-07-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-07-12 | 1990-01-11 | 1990-07-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-07-12 | 1994-01-11 | 1994-07-13 | $7700.00 | Window Closed / Lapsed |