# US 5,700,621 A · Polymers and photosensitive mixture prepared therewith

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- Number: US 5,700,621 A
- Document ID: US5700621A
- Status: Granted
- Kind: A
- Application number: 08/607,809
- Filed: 1996-02-28
- Granted: 1997-12-23
- Earliest claimed: 1995-03-04
- Assignees: Agfa-Gevaert
- Inventors: Mathias Eichhorn; Andreas Elsaesser
- Web page: https://patentgrep.com/patent/US5700621A

## CPC

- G03F 7/0233: {characterised by the polymeric binders or the macromolecular additives other than the macromolecular quinonediazides}
- C08F 20/60: containing nitrogen in addition to the carbonamido nitrogen
- 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)
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS

## Abstract

A polymer comprising repeating units of the formula ##STR1## wherein R.sup.1 , R.sup.2 and R.sup.3 are, independently of one another, hydrogen atoms or alkyl groups, X is CO or SO.sub.2, and Y and Z are, independently of one another, alkyl, alkenyl, cycloalkyl, aryl or heterocyclic radicals, or Y and Z are linked to one another and are constituents of a five-membered or six-membered hetero-cyclic ring.

## Claims

### Claim 1

A polymer comprising:
repeating units of formula I: ##STR7## wherein R.sup.1, R.sup.2 and R.sup.3 are, independently of one another, hydrogen atoms or alkyl groups,
X is CO or SO.sub.2, and
Y and Z are, independently of one another, alkyl, alkenyl, cycloalkyl, aryl, or heterocyclic radicals, or Y and Z are linked to one another and are constituents of a five-membered or six-membered heterocyclic ring; and
units containing acidic hydrogen atoms which are derived from sulfonic, carboxylic or phosphonic acids, sulfonamides, sulfonimides or carboximides or phenols.

### Claim 2 (depends on 1)

A polymer has claimed in claim 1, wherein R.sup.1 and R.sup.3 are hydrogen atoms.

### Claim 3 (depends on 1)

A polymer as claimed in claim 1, wherein R.sup.2 is a methyl group.

### Claim 4 (depends on 1)

A polymer as claimed in claim 1, wherein Y and Z are linked to form a five-membered ring to which a further ring is fused.

### Claim 5 (depends on 4)

A polymer as claimed in claim 4, wherein the further ring is a benzene ring.

### Claim 6 (depends on 1)

A polymer as claimed in claim 1, wherein said units of the formula I are present in an amount from 20-100% by weight based on the weight of the polymer.

### Claim 7

A method for the production of a polymer comprising:
repeating units of formula I: ##STR8## wherein R.sup.1, R.sup.2 and R.sup.3 are, independently of one another, hydrogen atoms or alkyl groups,
X is CO or SO.sub.2, and
Y and Z are, independently of one another, alkyl, alkenyl, cycloalkyl, aryl, or heterocyclic radicals, or Y and Z are linked to one another and are constituents of a five-membered or six-membered heterocyclic ring; and
units containing acidic hydrogen atoms which are derived from sulfonic, carboxylic or phosphonic acids, sulfonamides, sulfonimides or carboximides or phenols,
said method comprising reacting an unsaturated nitrile of formula: ##STR9## with an N-hydroxymethylimide of formula: ##STR10## in the presence of an acid to form a monomer of formula II ##STR11## and copolymerizing the monomer of the formula II and said units containing acidic hydrogen atoms in the presence of a free-radical-forming catalyst to form the polymer containing units of the formula I, and wherein
R.sup.1, R.sup.2 and R.sup.3 are, independently of one another, hydrogen atoms or alkyl groups,
X is CO or SO.sub.2, and
Y and Z are, independently of one another, alkyl, alkenyl, cycloalkyl, aryl, or heterocyclic radicals, or Y and Z are linked to one another and are constituents of a five-membered or six-membered heterocyclic ring.

### Claim 8 (depends on 7)

A method for the production of a polymer as claimed in claim 7, wherein R.sup.1 and R.sup.3 are hydrogen atoms.

### Claim 9 (depends on 7)

A method for the production of a polymer as claimed in claim 7, wherein R.sup.2 is a methyl group.

### Claim 10 (depends on 7)

A method for the production of a polymer as claimed in claim 7, wherein Y and Z are linked to form a five-membered ring to which a further ring is fused.

### Claim 11 (depends on 10)

A method for the production of a polymer as claimed in claim 10, wherein the further ring is a benzene ring.

### Claim 12 (depends on 7)

A method for the production of a polymer as claimed in claim 7, further comprising reacting monomer units containing acidic hydrogen atoms.

### Claim 13 (depends on 12)

A method for the production of a polymer as claimed in claim 12, wherein the units containing acidic hydrogen atoms are derived from sulfonic, carboxylic or phosphonic acids, sulfonamides, sulfonimides or carboximides or phenols.

### Claim 14 (depends on 7)

A method for the production of a polymer as claimed in claim 7, wherein said monomer units of the formula II are present in an amount from 20-100% by weight based on the weight of the polymer.

### Claim 15

A method for producing a photosensitive mixture comprising mixing
(a) a water-insoluble polymeric binder which is soluble or swellable in aqueous-alkaline solutions and
(b) a 1,2 quinone diazide, wherein the water-insoluble binder a) comprises a polymer comprising:
repeating units of formula I: ##STR12## wherein R.sup.1, R.sup.2 and R.sup.3 are independently of one another, hydrogen atoms or alkyl groups,
X is CO or SO.sub.2, and
Y and Z are independently of one another, alkyl, alkenyl, cycloalkyl, aryl, or heterocyclic radicals, or Y and Z are linked to one another and are constituents of a five-membered or six-membered heterocyclic ring; and units containing acidic hydrogen atoms which are derived from sulfonic, carboxylic or phosphonic acids, sulfonamides, sulfonimides or carboximides or phenols.

### Claim 16 (depends on 15)

A method for producing a photosensitive recording material comprising forming a base layer and a photosensitive layer, wherein the photosensitive layer comprises a photosensitive mixture as claimed in claim 15.