# US 4,399,259 A · Photocrosslinkable polymers with side groups derived from indenone and the preparation and use of these polymers

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- Number: US 4,399,259 A
- Document ID: US4399259A
- Status: Granted
- Kind: A
- Application number: 06/304,521
- Filed: 1981-09-21
- Granted: 1983-08-16
- Earliest claimed: 1979-01-30
- Assignees: Ciba-Geigy Corporation
- Inventors: Hans Zweifel; Joseph Berger; Hans Bosshard
- Web page: https://patentgrep.com/patent/US4399259A

## CPC

- C08F 20/30: containing aromatic rings in the alcohol moiety
- C08F 8/14: Esterification
- C08F 16/22: Carbocyclic compounds
- C08G 8/28: Chemically modified polycondensates
- C08G 85/004: {Modification of polymers by chemical after-treatment}
- C08F 2810/30: leading to the formation or introduction of aliphatic or alicyclic unsaturated groups
- 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

## Abstract

The invention relates to polymers which are crosslinkable under the action of light and contain side groups of the formula ##STR1## in which R.sup.3 is preferably chlorine and R, R.sup.1 and R.sup.2 are, for example, H or --CH.sub.3. The proportion of these groups in the polymers is preferably 20 to 100%. Because of their high sensitivity to light, these polymers are suitable for photographic applications.

## Claims

### Claim 1

A polymer, crosslinkable under the action of light, which has an average molecular weight between 1,000 and 1,000,000, as measured by the intrinsic viscosity of a solution of said polymer in N,N-dimethylformamide at 20.degree. C., and which has side groups of the formula I ##STR39## in which R.sup.3 is Cl or Br, and R, R.sup.1 and R.sup.2 are identical or different and R is a n-alkyl radical having 1 to 4 C atoms, or is H, Cl, Br or F, R.sup.1 is a n-alkyl radical having 1 to 4 C atoms, or is H, and R.sup.2 is H or CH.sub.3, or R.sup.1 and R.sup.2 together are the group --CH.sub.2 CH.sub.2 CH.sub.2 --, with the proviso that in the latter case the bond to the six-membered ring is via the C atoms in the 5-position and 6-position of the nucleus, the proportion of groups of the formula I being at least 5%, based on the number of recurring structural elements of the polymer, said polymer being a homopolymer or copolymer derived from monomers containing reactive C.dbd.C double bonds, wherein said polymer comprises
(a) from 5 to 100 percent, based on the number of recurring structural elements in the polymer chain, or molecular chain members selected from the group consisting of formulas II to VI. ##STR40## in which the radical E has the formula I, m is a number from 2 to 6, n is a number from 1 to 10 and R.sup.6 is H or --CH.sub.3, and
(b) from 95 to 0 percent, based on the number of recurring structural elements in the polymer chain, of structural elements of the formula IX ##STR41## in which X.sub.1 and X.sub.3 are each hydrogen, X.sub.2 is hydrogen, chlorine or methyl and X.sub.4 is hydrogen, methyl, chlorine, --CN, --COOH, phenyl, methylphenyl, methoxyphenyl, cyclohexyl, --COO--alkyl having 1-12 C atoms in the alkyl moiety, --COO--phenyl, ##STR42## --COO--alkyl--OH having 1-3 C atoms in the alkyl moiety, --OCO--alkyl having 1-4 C atoms in the alkyl, --OCO--phenyl, --CO--alkyl having 1-3 C atoms in the alkyl, alkoxy having 1-6 C atoms or phenoxy, or X.sub.1 and X.sub.2 are each hydrogen and X.sub.3 and X.sub.4 together are the grouping ##STR43## or are each --COOH or --COO--alkyl having 1-6 C atoms in the alkyl.

### Claim 2 (depends on 1)

A polymer according to claim 1 having an average molecular weight between 30,000 and 1,000,000.

### Claim 3 (depends on 1)

A polymer according to claim 1, in which the proportion of groups of the formula I is 20-100 percent, based on the number of recurring structural elements of the polymer.

### Claim 4 (depends on 1)

A polymer according to claim 1, which contains structural elements of the formula IX in which X.sub.1 and X.sub.3 are each hydrogen, X.sub.2 is hydrogen or methyl and X.sub.4 is --OCOCH.sub.3, --COOH or --COO--alkyl having 1-8 C atoms in the alkyl, or in which X.sub.1, X.sub.2 and X.sub.3 are each hydrogen and X.sub.4 is --CN, chlorine or phenyl.

### Claim 5 (depends on 1)

A polymer according to claim 1, which contains molecule chain members of the formula XVII ##STR44##

### Claim 6 (depends on 1)

A polymer according to claim 1, which contains molecule chain members of the formula XVIII ##STR45##

### Claim 7 (depends on 1)

A polymer according to claim 1, which contains molecule chain members of the formula XIX ##STR46##

### Claim 8 (depends on 1)

A polymer according to claim 1, which contains molecule chain members of the formula XX ##STR47##

### Claim 9 (depends on 1)

A polymer according to claim 1, which contains molecule chain members of the formula XXI ##STR48##
