# US 5,347,040 A · Sensitized onium salts

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- Number: US 5,347,040 A
- Document ID: US5347040A
- Status: Granted
- Kind: A
- Application number: 07/988,435
- Filed: 1992-12-09
- Granted: 1994-09-13
- Earliest claimed: 1992-12-09
- Assignees: E. I. Du Pont de Nemours and Company
- Inventors: Arnost Reiser; Xiaohua He
- Web page: https://patentgrep.com/patent/US5347040A

## CPC

- C07C 309/43: having at least one of the sulfo groups bound to a carbon atom of a six-membered aromatic ring being part of a condensed ring system
- C07C 381/12: Sulfonium compounds
- C08F 2/50: with sensitising agents
- C08G 59/68: characterised by the catalysts used
- C08G 65/105: {Onium compounds}
- Y10S 430/115: Cationic or anionic
- Y10S 430/127: Spectral sensitizer containing
- C07C: ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Onium salt capable of generating acid upon exposure to actinic radiation having the following structure: (R.sub.1).sub.a (R.sub.2).sub.b (R.sub.3).sub.c Q.sup.+ --A--M.sup.+ X.sup.- --B--X'.sup.- where: Q is S; R.sub.1, R.sub.2 and R.sub.3 are independently substituted or unsubstituted aromatic, aliphatic, or aralkyl groups having 7-18 carbon atoms; M.sup.+ is a cationic organic radical; A is a divalent radical selected from the group of hindered alkylene groups, substituted or unsubstituted aromatic or aralkyl groups; B is a divalent aromatic sensitizer which absorbs radiation having a wavelength longer than 300 nm and is capable of transferring an electron to Q, x.sup.- and X'.sup.- are anionic groups; and wherein A provides a spatial separation between Q and M, and B provides a spatial separation between X and X', such that the spatial separation provided by A between Q and M is substantially the same as the spatial separation provided by B between X and X'.

## Claims

### Claim 1

An onium salt capable of generating acid upon exposure to actinic radiation having the following structure:
(R.sub.1).sub.a (R.sub.2).sub.b (R.sub.3).sub.c Q.sup.+ --A--M.sup.+ X.sup.- --B--X'.sup.-
where:
Q is S;
R.sub.1, R.sub.2 and R.sub.3 are independently aromatic groups having 6-12 carbon atoms, which may be substituted with hydroxyl, alkoxyl, amino or alkylamino groups; or aliphatic groups having 1-12 carbon atoms, which may be substituted with hydroxyl, alkoxyl, amino or alkylamino groups; or aralkyl groups having 7-18 carbon atoms, which may be substituted with hydroxyl, alkoxyl, amino or alkylamino groups;
M.sup.+ is a cationic organic group having the structure:
Q'.sup.+ (R.sub.4).sub.d (R.sub.5).sub.e (R.sub.6).sub.f
where Q' is S;
R.sub.4, R.sub.5, and R.sub.6 are independently aromatic groups having 6-12 carbon atoms, which may be substituted with hydroxyl, alkoxyl, amino or alkylamino groups; or aliphatic groups having 1-12 carbon atoms, which may be substituted with hydroxyl, alkoxyl, amino or alkylamino groups; or aralkyl groups having 7-18 carbon atoms, which may be substituted with hydroxyl, alkoxyl, amino or alkylamino groups;
f=0;
d and e are 0, 1 or 2 such that d+e=2 when R.sub.4 and R.sub.5 are monovalent groups; and d+e=1 when R.sub.4 or R.sub.5 is a divalent group;
A is a divalent group selected from the group of hindered alkylene groups having 4-12 carbon atoms; aromatic groups having 6-18 carbon atoms, which may be substituted with hydroxyl, alkoxyl, amino or alkylamino groups; and aralkyl groups having 7-24 carbon atoms, which may be substituted with hydroxyl, alkoxyl, amino or alkylamino groups;
B is a divalent aromatic sensitizer which absorbs radiation having a wavelength longer than 300 nm and is capable of transferring an electron to Q,
x.sup.- and X'.sup.- are anionic groups independently selected from the group consisting of sulfate, sulfonate, sulfite phosphate, phosphite and carboxylate; and when
c=0;
a and b=0, 1, or 2 such that a+b=2 when R.sub.1 and R.sub.2 are monovalent groups;
and a+b=1 when R.sub.1 or R.sub.2 is a divalent group;
wherein A provides a spatial separation between Q and M, and B provides a spatial separation between X and X', such that the spatial separation provided by A between Q and M is substantially the same as the spatial separation provided by B between X and X'.

### Claim 2 (depends on 1)

The onium salt of claim 1 wherein B is selected from the group consisting of anthracene, benzoflavin, perylene, ruberene, benzophenone, anthraquinone, pyrene, anthrone and thioxanthone.

### Claim 3 (depends on 1)

The onium salt of claim 1 wherein R.sub.1, R.sub.2, R.sub.4, and R.sub.5 are phenyl groups; A is 4,4'-biphenyl; B is 2,6-(9,10-diacetyloxy anthracene); and X.sup.- =X'.sup.- =SO.sub.3.sup.-.