# US 5,703,142 A · Photo-curable prepolymer comprising quaternary ammonium salt and process for preparing thereof

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- Number: US 5,703,142 A
- Document ID: US5703142A
- Status: Granted
- Kind: A
- Application number: 08/534,713
- Filed: 1995-09-27
- Granted: 1997-12-30
- Earliest claimed: 1994-09-27
- Assignees: Hanwha Chemical Corporation
- Inventors: Sang-Keun Kim; Haeng-Woo Lee; Cheol-Kyu Choi; Jeong-Deuk Kim; Jin-Who Hong; Chang-Soo Kim; Kong-Hyun Whang
- Web page: https://patentgrep.com/patent/US5703142A

## CPC

- C08F 20/36: containing oxygen in addition to the carboxy oxygen {, e.g. 2-N-morpholinoethyl (meth)acrylate or 2-isocyanatoethyl (meth)acrylate}
- C07D 251/34: Cyanuric or isocyanuric esters
- C08F: MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C07D: HETEROCYCLIC COMPOUNDS (macromolecular compounds C08)

## Abstract

The present invention relates to a photo-curable prepolymer having the following formula (I): ##STR1## in which W represents ##STR2## R.sub.1 represents hydrogen or methyl; R.sub.1 ' represents ##STR3## wherein X represents chlorine or bromine atom, R.sub.2 represents methyl or ethyl, n, o and q independently of one another denote an integer of 1 to 6 and p denotes an integer of 0 to 6; R.sub.2 ' and R.sub.3 ' are identical to or different from each other and represent ##STR4## wherein L denotes an integer of 0 to 5, or ##STR5## wherein m denotes an integer of 1 to 6; a, b and c independently of one another represent a real number of 3 or less, provided that they satisfy the conditions of 0<a.ltoreq.3, 0.ltoreq.b and/or c<3 and a+b+c=3. which shows permanent antistatic property by introducing therein an acrylate moiety having quaternary ammonium group and hydroxy group simultaneously, and to a process for preparing thereof.

## Claims

### Claim 1

A photo-curable prepolymer having the following formula (I) ##STR12## in which W represents ##STR13## R.sub.1 represents hydrogen or methyl; R.sub.1 ' represents ##STR14## wherein X represents a chlorine or bromine atom, R.sub.2 represents methyl or ethyl, n, o and q independently of one another denote an integer of 1 to 6 and p denotes an integer of 0 to 6;
R.sub.2 ' and R.sub.3 ' are identical to or different from each other and represent ##STR15## wherein L denotes an integer of 0 to 5, or ##STR16## wherein m denotes an integer of 1 to 6; a, b and c independently of one another represent a real number of 3 or less, provided that they satisfy the conditions of
< a.ltoreq.3, 0.ltoreq.b<3 and 0.ltoreq.c<3 and a+b+c=3.
2.

### Claim 2 (depends on 1)

A process for preparing the photo-curable prepolymer of formula (I) as defined in claim 1, comprising reacting an aliphatic multifunctional isocyanate having the following formula (II) ##STR17## with at least one quaternary ammonium salt selected from salts having the following formulae (III), (IV) and (v): ##STR18## ##STR19## wherein R.sub.1, R.sub.1 ', R.sub.2 ' and R.sub.3 ' are defined as described in claim 1.

### Claim 3 (depends on 2)

The process according to claim 2, wherein the salt of the formula (IV) or (V) is selected from the group consisting of hydroxyethyl acrylate, hydroxyethyl methacrylate, hydroxypropyl acrylate, hydroxypropyl methacrylate and hydroxypolyester acrylate.

### Claim 4 (depends on 2)

The process according to claim 2, wherein the hydroxy group in the compound of formula (III) is used in a ratio of 1/10 to 2/3 equivalents with respect to the isocyanate groups in the compound of formula (II).

### Claim 5 (depends on 4)

A cured resin film made by the process of claim 4 and having a surface resistance of from 10.sup.11 to 10.sup.13 .OMEGA. and an electrostatic decay time of from 0.1 to 0.5 milliseconds.

### Claim 6 (depends on 1)

A method for preparing a cured resin film having antistatic properties, comprising:
(i) coating a substrate with a resin composition comprising a prepolymer according to claim 1; and
(ii) photo-curing said resin composition; to obtain a cured resin film having a surface resistance of from 10.sup.11 to 10.sup.13 .OMEGA. and an electrostatic decay time of from 0.1 to 0.5 milliseconds.