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US4398014A Expired / Lapsed US ⏱️ 0.0 years remaining

Sulfoxonium salts and their use as polymerization catalysts

Assignee: BASF Corp
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Filing: 1981-10-23
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Granted: 1983-08-09
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Expires: 2001-10-23
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Abstract

Abstract New aromatic sulfonylsulfoxonium salts are of formula ##STR1## where q is 1 to 4, R denotes an aliphatic, cycloaliphatic, or aromatic group, R 6 denotes H, an alkyl or aralkyl group, or a group --COR 9 , --CO--NH--(CO) r --R 10 , or --SO 2 --R 11 , where r is zero or 1, one, but not both, of R and R 6 denoting an aromatic group, R 7 denotes an alkyl, alkenyl, cycloalkyl, cycloalkylalkyl, or aralkyl group, R 8 has the same meaning as R 7 but may alternatively represent a dialkylamino group or, if R 7 denotes alkyl, it may alternatively represent an arylamino group, R 9 , R 10 , and R 11 each denote an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms, t is 1, 2, or 3, and Z - denotes a t-valent anion of a protic acid. The salts, e.g., dimethyl-p-toluenesulfonylmethylsufoxonium hexafluorophosphate, are useful as catalysts for the polymerization of cationically polymerizable materials by means of actinic radiation and/or heat. Polyepoxides and resols may be photopolymerized in the presence of the salts and subsequently crosslinked with a latent heat-curing agent.

Inventors

  • 👤 George E. Green
  • 👤 Edward Irving
  • 👤 Bernard P. Stark

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-27 20:58
CPC Classifications
G; G03; G03F; G03F7/00; G03F7/004; G03F7/027; G03F7/028; G03F7/029; C; C07; C07C; C07C381/00; C08; C08G; C08G59/00; C08G59/18; C08G59/68; C08G59/687; C08G65/00; C08G65/02; C08G65/04; C08G65/06; C08G65/08; C08G65/10; C08G65/105; C08G85/00; C08K; C08K5/00; C08K5/36; C08K5/41; C08K5/42

Claims Analysis

Total Claims: 15
Claim 1
Independent Claim 394 words
A polymerizable composition which comprises (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 an aromatic sulfonylsulfoxonium salt of the formula ##STR16## where q is an integer of from 1 to 4, R denotes an aliphatic, cycloaliphatic or aromatic group of valency q, having from 1 to 25 carbon atoms and being directly linked through a carbon atom thereof to the sulfur atom of the indicated adjacent sulfonyl group, R 6 denotes a hydrogen atom, an alkyl or aralkyl group of 1 to 25 carbon atoms, an acyl group of formula --COR 9 or a group of formula --CO--NH--(CO).sub.r --R.sup.10 VII or ##STR17## one, but not both, of R and R 6 denoting a homocyclic aromatic group of 6 to 25 carbon atoms or a heterocyclic aromatic group of 4 to 25 carbon atoms containing one or more nitrogen, oxygen or sulfur atoms in the aromatic ring, R 7 denotes an alkyl group of 1 to 12 carbon atoms, an alkenyl group of 2 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms, a cycloalkylalkyl group of 4 to 10 carbon atoms, an aryl group of 6 to 24 carbon atoms, or an aralkyl group of 7 to 16 carbon atoms, R 8 has the same meaning as R 7 , or R 8 is a dialkylamino group of 2 to 6 carbon atoms, or if R 7 is alkyl of 1 to 12 carbon atoms, R 8 may also be an arylamino group of 6 to 8 carbon atoms, R 9 denotes an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms, directly linked through a carbon atom thereof to the indicated --CO-- group, r is zero or 1, R 10 denotes an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms, directly linked through a carbon atom thereof to, if r denotes zero, the indicated nitrogen atom, or if r denotes 1, the carbon atom of the indicated adjacent carbonyl group, R 11 denotes an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms, directly linked through a carbon atom thereof to the indicated sulfur atom, t represents 1, 2, or 3, and Z t- denotes a t-valent anion of a protic acid.
Claim 2
Dependent Claim 394 words
A polymerizable composition which comprises (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 an aromatic sulfonylsulfoxonium salt of the formula ##STR16## where q is an integer of from 1 to 4, R denotes an aliphatic, cycloaliphatic or aromatic group of valency q, having from 1 to 25 carbon atoms and being directly linked through a carbon atom thereof to the sulfur atom of the indicated adjacent sulfonyl group, R 6 denotes a hydrogen atom, an alkyl or aralkyl group of 1 to 25 carbon atoms, an acyl group of formula --COR 9 or a group of formula --CO--NH--(CO).sub.r --R.sup.10 VII or ##STR17## one, but not both, of R and R 6 denoting a homocyclic aromatic group of 6 to 25 carbon atoms or a heterocyclic aromatic group of 4 to 25 carbon atoms containing one or more nitrogen, oxygen or sulfur atoms in the aromatic ring, R 7 denotes an alkyl group of 1 to 12 carbon atoms, an alkenyl group of 2 to 6 carbon atoms, a cycloalkyl group of 3 to 8 carbon atoms, a cycloalkylalkyl group of 4 to 10 carbon atoms, an aryl group of 6 to 24 carbon atoms, or an aralkyl group of 7 to 16 carbon atoms, R 8 has the same meaning as R 7 , or R 8 is a dialkylamino group of 2 to 6 carbon atoms, or if R 7 is alkyl of 1 to 12 carbon atoms, R 8 may also be an arylamino group of 6 to 8 carbon atoms, R 9 denotes an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms, directly linked through a carbon atom thereof to the indicated --CO-- group, r is zero or 1, R 10 denotes an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms, directly linked through a carbon atom thereof to, if r denotes zero, the indicated nitrogen atom, or if r denotes 1, the carbon atom of the indicated adjacent carbonyl group, R 11 denotes an alkyl, aryl, or aralkyl radical of 1 to 25 carbon atoms, directly linked through a carbon atom thereof to the indicated sulfur atom, t represents 1, 2, or 3, and Z t- denotes a t-valent anion of a protic acid.
Claim 3
Dependent Claim 25 words
A composition according to claim 1, in which R represents a monocyclic or dicyclic homocyclic aryl or aralkyl group of 6 to 16 carbon atoms.
Claim 4
Dependent Claim 24 words
A composition according to claim 1, in which R represents a monocyclic or dicyclic arylene or aralkylene group of 6 to 16 carbon atoms.
Claim 5
Dependent Claim 81 words
A composition according to claim 1, in which R 7 and R 8 are each an alkyl group of 1 to 4 carbon atoms, a phenyl group, a naphthyl group, or a phenyl or a naphthyl group substituted in the aromatic ring or rings by one or two alkyl groups, each of 1 to 4 carbon atoms, or 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 26 words
A composition according to claim 1, in which R denotes an aromatic group and R 9 denotes an aliphatic radical of 1 to 8 carbon atoms.
Claim 7
Dependent Claim 26 words
A composition according to claim 1, in which R denotes an aromatic group and R 10 denotes an aliphatic radical of 1 to 8 carbon atoms.
Claim 8
Dependent Claim 26 words
A composition according to claim 1, in which R denotes an aromatic group and R 11 denotes an aliphatic radical of 1 to 8 carbon atoms.
Claim 9
Dependent Claim 16 words
A composition according to claim 1, wherein Z t- denotes an anion of an inorganic acid.
Claim 10
Dependent Claim 114 words
A composition according to claim 1, where Z t- denotes Cl - , Br - , NO 3 - , HSO 4 - , HSO 3 - , ClO 4 - , CF 3 SO 3 - , CF 3 COO - , CH 3 C 6 H 4 SO 3 - , H 2 PO 4 - , SO 4 -- , PO 4 --- , SbF 5 (OH) - , or an anion of formula MX.sub.n.sup.- XI where M denotes an atom of antimony, bismuth, boron, arsenic, or phosphorus, X denotes a fluorine or chlorine atom, and n is 4, 5, or 6 and is one more than the valency of m.
Claim 11
Dependent Claim 18 words
A composition according to claim 1, in which (b) is dimethyl-p-toluenesulfonylmethylsulfoxonium hexafluorophosphate, dimethyltoluene-p-sulfonylmethylsulfoxonium hexafluoroantimonate, tris(dimethyltoluene-p-sulfonylmethylsulfoxonium)orthophosphate, or dimethylphenylsulfonylmethylsulfoxonium hexafluorophosphate.
Claim 12
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 13
Dependent Claim 23 words
A composition according to claim 1, wherein (a) is either an epoxide resin or a resol made from a phenol and an aldehyde.
Claim 14
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 15
Dependent Claim 23 words
A composition according to claim 12, which also contains a curing amount of a latent heat-curing agent for epoxide resins or resol resins.

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1986-08-08 1987-02-07 1987-08-09 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1990-08-08 1991-02-07 1991-08-09 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1994-08-08 1995-02-07 1995-08-09 $7700.00 Window Closed / Lapsed

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