# US 4,496,643 A · Two-component dry electrostatic developer composition containing onium charge control agent

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- Number: US 4,496,643 A
- Document ID: US4496643A
- Status: Granted
- Kind: A
- Application number: 06/592,996
- Filed: 1984-03-23
- Granted: 1985-01-29
- Earliest claimed: 1984-03-23
- Assignees: Eastman Kodak Company
- Inventors: John C. Wilson; Lawrence P. DeMejo; Thomas A. Jadwin; Stewart H. Merrill
- Web page: https://patentgrep.com/patent/US4496643A

## CPC

- G03G 9/09741: {cationic}
- G03G 9/09783: {Organo-metallic compounds}
- G03G 9/1134: {containing fluorine atoms}
- G03G: ELECTROGRAPHY; ELECTROPHOTOGRAPHY; MAGNETOGRAPHY

## Abstract

A two-component, dry electrostatic developer composition containing toner particles and coated-carrier particles is disclosed. The toner contains a binder polymer and a phosphonium, arsonium or stibonium charge-control agent dispersed in the toner binder. The carrier is coated with a fluoropolymer. The resulting developer exhibits reduced toner throw-off and other disclosed advantages.

## Claims

### Claim 1

A dry, two-component electrostatic developer composition comprising:
(a) toner particles comprising a polymeric binder,
(b) an onium compound, as a charge-control agent, dispersed in the toner binder and having the formula: ##STR3## wherein: X is a phosphorous, arsenic or antimony atom;
each of R.sub.2, R.sub.3 and R.sub.4, which are the same or different, represents alkyl having from 1 to about 20 carbon atoms; aralkyl or alkaryl in which the alkyl group has 1 to about 20 carbon atoms and the aryl group has from about 6 to about 14 carbon atoms; or aryl having from about 6 to about 14 carbon atoms;
R.sub.1 represents a group as defined with respect to R.sub.2, R.sub.3 and R.sub.4 ; a hetero ring system when taken together with X and any one of R.sub.2, R.sub.3 and R.sub.4 ; or the group: ##STR4## wherein: R.sub.5 is alkylene having from about 1 to about 20 carbon atoms; oxydialkylene having from about 1 to about 20 carbon atoms in each alkylene group or dialkylenearylene having from about 1 to about 20 carbon atoms in each alkylene group and from about 6 to about 14 atoms in the arylene group; and
Y.sup.- is an anion, and
(c) carrier particles surface-coated with a fluoropolymer.

### Claim 2 (depends on 1)

The developer of claim 1 wherein each of R.sub.2, R.sub.3 and R.sub.4 is optionally substituted aryl, or optionally substituted 2- to 5-carbon alkyl.

### Claim 3 (depends on 1)

The developer of claim 1 wherein the fluoropolymer coating on the carrier is a polymer selected from the group consisting of perfluoroalkoxy fluoropolymers, poly(tetrafluoroethylene), poly(vinylidene fluoride), poly(vinylidene fluoride-co-tetrafluoroethylene), polyvinyl fluoride, and poly(hexafluoropropylene-tetrafluoroethylene).

### Claim 4 (depends on 1)

A developer as in claim 1 wherein the charge-control agent is selected from the group consisting of:
1 benzyltriphenylphosphonium chloride;
2 methyltriphenylphosphonium bromide;
3 tetrabutylphosphonium bromide;
4 dodecyltributylphosphonium bromide;
5 phthalimidomethyltributylphosphonium bromide;
6 octadecyltributylphosphonium bromide;
7 methyltriphenylphosphonium fluoroborate;
8 ethyltriphenylphosphonium fluoroborate;
9 methyltriphenylphosphonium hexafluorophosphate;
10 dodecyltributylphosphonium p-toluenesulfonate;
11 bis(4-carbomethoxyphenyl)methylphenylphosphonium p-toluenesulfonate;
12bis(4-hydroxypropyl)methylphenylphosphonium p-toluenesulfonate;
13 bis(4-acetoxyphenyl)methylphenylphosphonium p-toluenesulfonate;
14 tris(4-acetoxyphenyl)methylphosphonium p-toluenesulfonate;
15 methyltriphenylphosphonium p-toluenesulfonate;
16 dodecyltriphenylphosphonium p-toluenesulfonate;
17 methyltriphenylphosphonium benzenesulfonate;
18 ethyltriphenylphosphonium p-toluenesulfonate;
19 phenethyltriphenylphosphonium p-toluenesulfonate;
20 ethylene-bis(triphenylphosphonium p-toluenesulfonate);
21 methyltriphenylphosphonium tetraphenylborate;
22 tris(methoxyphenyl)methylphosphonium p-toluenesulfonate;
23 methyltritolylphosphonium p-toluenesulfonate;
24 tris(chlorophenyl)methylphosphonium p-toluenesulfonate;
25 tris(carbomethoxyphenyl)methylphosphonium p-toluenesulfonate;
26 benzyltriphenylphosphonium phosphomolybdate;
27 benzyltriphenylphosphonium silicotungstate;
28 methyltriphenylphosphonium phosphomolybdate;
29 benzyltriphenylphosphonium phosphotungstate;
30 methyl 4-carbomethoxyphenyldiphenylphosphonium p-toluenesulfonate;
31 methyl 4-acetoxyphenyldiphenylphosphonium p-toluenesulfonate;
32 methyl 3,5-biscarbomethoxyphenyldiphenylphosphonium p-toluenesulfonate;
33 (m+p)vinylbenzyltriphenylphosphonium p-toluenesulfonate;
34 methyltriphenylarsonium p-toluenesulfonate; and
35 methyltriphenylantimonium p-toluenesulfonate.

### Claim 5 (depends on 2)

The developer of claim 2 wherein said charge-control agent is methyltriphenylphosphonium tetrafluoroborate, methyltriphenylphosphonium p-toluenesulfonate, or bis(p-carbomethoxypheny)phenylmethylphosphonium p-toluene sulfonate.

### Claim 6 (depends on 1, 2, 3, 4, 5)

The developer of claim 1, 2, 3, 4 or 5 wherein the carrier comprises a magnetic material.

### Claim 7 (depends on 6)

The developer of claim 6 wherein the magnetic material is a hard magnetic material having a coercivity of at least 100 gauss at magnetic saturation.

### Claim 8 (depends on 6)

The developer of claim 6 wherein the concentration of the charge-control agent is from about 0.5 to about 5.0 parts by weight charge-control agent per 100 parts by weight toner resin.

### Claim 9 (depends on 6)

The developer of claim 6 wherein the charge of the developer is from about 9 to about 35 microcoulombs per gram of toner in the developer.