# US 8,785,515 B2 · Sensitizer for cationic photoinitiators

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- Number: US 8,785,515 B2
- Document ID: US8785515B2
- Status: Granted
- Kind: B2
- Application number: 12/598,113
- Filed: 2008-05-09
- Published: 2010-05-27
- Granted: 2014-07-22
- Earliest claimed: 2007-05-11
- Assignees: Sun Chemical Corporation
- Applicants: Shaun Lawrence Herlihy; Robert Stephen Davidson
- Inventors: Shaun Lawrence Herlihy; Robert Stephen Davidson
- Web page: https://patentgrep.com/patent/US8785515B2

## CPC

- C07D 317/36: Alkylene carbonates; Substituted alkylene carbonates
- C08G 59/68: characterised by the catalysts used
- C08G 65/105: {Onium compounds}
- C09D 11/101: Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
- C09D 163/00: Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
- C09D 171/02: Polyalkylene oxides
- C09J 171/02: Polyalkylene oxides
- G03F 7/038: Macromolecular compounds which are rendered insoluble or differentially wettable (G03F7/075 takes precedence; macromolecular azides G03F7/012; macromolecular diazonium compounds G03F7/021)
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09D: COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR (cosmetics A61K; processes for applying liquids or other fluent materials to surfaces, in general, B05D; staining wood B27K5/02; glazes or vitreous enamels C03C; natural resins, French polish, drying-oils, driers, turpentine, per se, C09F; polishing compositions other than French polish, ski waxes C09G; adhesives or use of materials as adhesives C09J; materials for sealing or packing joints or covers C09K3/10; materials for stopping leaks C09K3/12; processes for the electrolytic or electrophoretic production of coatings C25D)
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- G03F: PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR; (phototypographic composing devices B41B; photosensitive materials or processes for photographic purposes G03C; electrophotography, sensitive layers or processes therefor G03G)

## Abstract

Polycyclic aromatic compounds of formula (I) having at least two conjugated aromatic rings at least one of which has a substituent comprising a cyclic carbonate group can be used as sensitizers for cationic photoinitiators, especially iodonium compounds, and may also function as monomers in cationically initiated radiation curable compositions, especially coating compositions, such as printing inks and varnishes.

## Claims

### Claim 1

A composition comprising an iodonium salt cationic photoinitiator and a polycyclic aromatic compound having the formula (I):
in which:
Q represents a residue of a polycyclic aromatic compound having at least two conjugated aromatic rings and having a valency x;
Y is an aliphatic carbon chain which may be interrupted by one or more oxygen atoms, sulphur atoms, phenylene groups, carbonyl groups, epoxide groups or linear or cyclic carbonate groups;
p is 0 or 1;
R1 and R2 are the same as or different from each other, and each represents a hydrogen atom, an alkyl group, a hydroxyalkyl group, an alkoxyalkyl group, an alkoxycarbonylalkyl group or a C2-C5 carbon chain which is attached to a carbon atom of Y to form a fused ring;
R1 represents a hydrogen atom or an alkyl group; and
m and n are the same as or different from each other, and each is zero or a number from 1 to 4, provided that (m+n) is zero or a number from 1 to 4.

### Claim 2 (depends on 1)

A composition according to claim 1, in which R3 is H, Y is Y1, p is 1, and x is 2 thereby having the formula (Ia):
in which Y1 represents an aliphatic group having from 1 to 3 carbon atoms.

### Claim 3 (depends on 2)

A composition according to claim 2, in which Y1 represents a methylene group.

### Claim 4 (depends on 1)

A composition according to claim 1, in which the conjugated aromatic rings of Q are fused rings.

### Claim 5

A composition according to 4, in which the conjugated aromatic ring is a naphthalene or anthracene ring system, which is substituted or unsubstituted.

### Claim 6 (depends on 1)

A composition according to claim 1, in which: Q represents a residue of an anthracene or naphthalene ring system, which is unsubstituted or has at least one alkyl substituent; m+n=1; R1, R2 and R3 all represent hydrogen atoms; Y is Y1—O—; and Y1 represents an alkylene group having from 1 to 3 carbon atoms.

### Claim 7 (depends on 2)

A composition according to claim 2, in which: Q represents a residue of an anthracene or naphthalene ring system, which is unsubstituted or has at least one alkyl substituent; m+n=1; R1 and R2 both represent hydrogen atoms; and Y1 represents an alkylene group having from 1 to 3 carbon atoms.

### Claim 8 (depends on 1)

A composition according to claim 1, in which the conjugated aromatic ring is biphenyl.

### Claim 9 (depends on 1)

A composition according to claim 1, in which the polycyclic aromatic compound is:

### Claim 10 (depends on 1)

A composition according to claim 1, in which the polycyclic aromatic compound is:

### Claim 11 (depends on 1)

A composition according to claim 1, further comprising a cationically polymerisable monomer or oligomer.

### Claim 12 (depends on 11)

A composition according to claim 11, in which the polycyclic aromatic compound comprises from 1 to 50% by weight of the total polymerisable components of the composition.

### Claim 13 (depends on 11)

A composition according to claim 11, in which the polycyclic aromatic compound comprises from 0.5 to 3% by weight of the total composition.

### Claim 14 (depends on 11)

A composition according to claim 11, formulated as a coating composition.

### Claim 15 (depends on 11)

A composition according to claim 11, formulated as a printing ink.

### Claim 16 (depends on 11)

A composition according to claim 11, formulated as an inkjet ink.

### Claim 17 (depends on 11)

A composition according to claim 11, formulated as an adhesive, release coating or primer.

### Claim 18 (depends on 11)

A process for preparing a cured coating composition, which comprises applying a composition according to claim 11 to a substrate and exposing the coated substrate to curing radiation sufficient to cure the coating.

### Claim 19 (depends on 18)

A process according to claim 18, in which the curing radiation is ultraviolet.

### Claim 20 (depends on 2)

A composition according to claim 2 having the formula (Ia) in which Y1 represents an alkylene group having from 1 to 3 carbon atoms.
