# US 5,705,308 A · Infrared-sensitive, negative-working diazonaphthoquinone imaging composition and element

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- Number: US 5,705,308 A
- Document ID: US5705308A
- Status: Granted
- Kind: A
- Application number: 08/723,335
- Filed: 1996-09-30
- Granted: 1998-01-06
- Earliest claimed: 1996-09-30
- Assignees: Eastman Kodak Company
- Inventors: Paul Richard West; Eugene Lynn Sheriff; Jeffrey Allen Gurney; Ralph Scott Schneebeli; Thomas Robert Jordan; Gary Roger Miller
- Web page: https://patentgrep.com/patent/US5705308A

## CPC

- B41C 1/1008: {by removal or destruction of lithographic material on the lithographic support, e.g. by laser or spark ablation; by the use of materials rendered soluble or insoluble by heat exposure, e.g. by heat produced from a light to heat transforming system; by on-the-press exposure or on-the-press development, e.g. by the fountain of photolithographic materials}
- G03F 7/0226: {characterised by the non-macromolecular additives}
- G03F 7/2022: {Multi-step exposure, e.g. hybrid; backside exposure; blanket exposure, e.g. for image reversal; edge exposure, e.g. for edge bead removal; corrective exposure}
- B41C 2210/04: Negative working, i.e. the non-exposed (non-imaged) areas are removed
- B41C 2210/06: Developable by an alkaline solution
- B41C 2210/24: characterised by a macromolecular compound or binder obtained by reactions involving carbon-to-carbon unsaturated bonds, e.g. acrylics, vinyl polymers
- B41C 2210/262: Phenolic condensation polymers, e.g. novolacs, resols
- Y10S 430/145: Infrared
- B41C: PROCESSES FOR THE MANUFACTURE OR REPRODUCTION OF PRINTING SURFACES (photomechanical processes for producing printing surfaces G03F; photoelectrical processes for producing printing surfaces G03G)
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

An infrared imaging composition contains two essential components, namely an infrared absorbing compound, and a phenolic resin that is either mixed or reacted with an o-diazonaphthoquinone derivative. These compositions are useful in photosensitive elements such as lithographic printing plates that can be adapted to direct-to-plate imaging procedures.

## Claims

### Claim 1

A negative-working photosensitive composition consisting essentially of:
a) (i) a mixture of a phenolic resin and an o-diazonaphthoquinone derivative,
(ii) a reaction product of a resin and an o-diazonaphthoquinone reactive derivative, or
(iii) a mixture of (i) and (ii), and
b) a compound that absorbs infrared radiation having a maximum absorption wavelength greater than about 750 nm, said compound being 2-›2-›2-chloro-3-›(1,3-dihydro-1,1,3-trimethyl-2H-benz›e!indol-2-ylidene)e thylidene-1-cyclohexen-1-yl!ethenyl!-1,1,3-trimethyl-1H-benz›e!indolium, salt with 4-methylbenzenesulfonic acid.

### Claim 2 (depends on 1)

The composition of claim 1 wherein a) is said reaction product (ii).

### Claim 3 (depends on 1)

The composition of claim 1 wherein said phenolic resin is a novolac resin.

### Claim 4 (depends on 1)

The composition of claim 1 wherein said o-diazonaphthoquinone reactive derivative is a sulfonic acid or carboxylic acid ester of o-diazonaphthoquinone.

### Claim 5

The composition of claim i wherein said o-diazonaphthoquinone derivative is 2,4-bis(2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy)benzophenone, 2 -diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy-2,2-bis(hydroxyphenyl)pro pane monoester, the hexahydroxybenzophenone hexaester of 2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonic acid, 2,2'-bis(2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy)biphenyl, 2,2',4,4'-tetrakis(2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy)biph enyl, 2,3,4-tris(2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy)benzophenone , 2,4-bis(2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy)benzophenone, 2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy-2,2-bis hydroxyphenylpropane monoester, the hexahydroxybenzophenone hexaester of 2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonic acid, 2,2'-bis(2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy)biphenyl, 2,2',4,4'-tetrakis(2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy)biph enyl or 2,3,4-tris(2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy)benzophenone

### Claim 6 (depends on 1)

The composition of claim 1 wherein the o-diazonaphthoquinone reactive derivative in said mixture has a non-polymeric ballast group having a molecular weight of at least about 15.

### Claim 7 (depends on 1)

The composition of claim 1 wherein said infrared radiation absorbing compound is present in an amount sufficient to provide an optical density of at least 0.5.

### Claim 8 (depends on 7)

The composition of claim 7 wherein said infrared radiation absorbing compound is present in an amount sufficient to provide an optical density of from about 1 to about 3.

### Claim 9

A photosensitive element consisting essentially of a support having thereon a negative-working photosensitive layer consisting essentially of:
a) (i) a mixture of a phenolic resin and an o-diazonaphthoquinone derivative,
(ii) a reaction product of a resin and an o-diazonaphthoquinone reactive derivative, or
(iii) a mixture of (i) and (ii), and
b) a compound that absorbs infrared radiation having a maximum absorption wavelength greater than about 750 nm, said compound being 2-›2-›2-chloro-3-›(1,3-dihydro-1,1,3-trimethyl-2H-benz›e!indol-2-ylidene)e thylidene-1-cyclohexen-1-yl!ethenyl!-1,1,3-trimethyl-1H-benz›e!indolium, salt with 4-methylbenzenesulfonic acid.

### Claim 10 (depends on 9)

The element of claim 9 wherein said support is a polyester film.

### Claim 11 (depends on 9)

The element of claim 9 wherein said support is a sheet of grained and anodized aluminum.

### Claim 12 (depends on 9)

The element of claim 9 wherein a) is reaction product (ii) wherein said resin is a novolac resin or a hydroxystyrene polymer.

### Claim 13 (depends on 9)

The element of claim 9 wherein said phenolic resin is a phenol-formaldehyde novolac resin.

### Claim 14 (depends on 9)

The element of claim 9 wherein said o-diazonaphthoquinone derivative is sulfonic acid or carboxylic acid ester of o-diazonaphthoquinone.

### Claim 15 (depends on 9)

The element of claim 9 wherein said o-diazonaphthoquinone derivative is 2,4-bis(2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy)benzophenone, 2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy-2,2-bis hydroxyphenylpropane monoester, the hexahydroxybenzophenone hexaester of 2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonic acid, 2,2'-bis(2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy)biphenyl, 2,2',4,4'-tetrakis(2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy)biph enyl, 2,3,4-tris(2-diazo-1,2-dihydro-1-oxo-5-naphthalenesulfonyloxy)benzophenone , 2,4-bis(2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy)benzophenone, 2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy-2,2-bis hydroxyphenylpropane monoester, the hexahydroxybenzophenone hexaester of 2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonic acid, 2,2'-bis(2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy)biphenyl, 2,2',4,4'-tetrakis(2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy)biph enyl or 2,3,4-tris(2-diazo-1,2-dihydro-1-oxo-4-naphthalenesulfonyloxy)benzophenone .

### Claim 16 (depends on 9)

The element of claim 9 wherein said infrared radiation absorbing compound is present in an amount sufficient to provide an optical density of at least about 0.5.

### Claim 17 (depends on 9)

The element of claim 9 wherein said infrared radiation absorbing compound is present in said photosensitive layer in an amount of at least 1 weight percent, said o-diazonaphthoquinone moiety is present in said photosensitive layer in an amount of at least about 1 weight percent, and
wherein a) is a mixture of said phenolic resins and said o-diazonaphthoquinone derivative, the weight ratio of said phenolic resin to said derivative in said photosensitive layer is at least about 0.5:1.

### Claim 18 (depends on 17)

The element of claim 17 wherein said infrared radiation absorbing compound is present in said photosensitive layer in an amount of from about 5 to about 25 weight percent, said o-diazonaphthoquinone moiety is present in said photosensitive layer in an amount of from about 3 to about 50 weight percent, and
wherein a) is a mixture of said phenolic resins and said o-diazonaphthoquinone derivative, the weight ratio of said phenolic resin to said derivative in said photosensitive layer is from about 2:1 to about 6:1.

### Claim 19

A lithographic printing plate consisting essentially of a grained and anodized aluminum support having thereon, as the outer layer, a single negative-working layer comprising a photosensitive composition consisting essentially of a reaction product of a phenol-formaldehyde novolak resin and 2-diazo-1,2-dihydro-1-oxo-4 or -5-naphthalenesulfonyl chloride, and 2-›2-›2-chloro-3-›(1,3-dihydro-1,1,3-trimethyl-2H-benz›e!indol-2-ylidene)e thylidene-1-cyclohexen-1-yl!ethenyl!-1,1,3-trimethyl-1H-benz›e!indolium, salt with 4-methylbenzenesulfonic acid.