Electrostatic toners containing aminodiacetic acid derivatives

Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Post imaging process – finishing – or perfecting composition...

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430137, G03G 9097

Patent

active

056630280

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel electrostatic toners containing a polymeric binder and, as a charge stabilizer, a compound of the formula I ##STR2## where
M.sup..sym. is one equivalent of a cation and
R is C.sub.1 -C.sub.21 -alkyl, which is unsubstituted or substituted by carboxyl or phenyl which may be substituted by C.sub.1 -C.sub.10 -alkyl, hydroxyl or a radical of the formula L--N(CH.sub.2 --COO.sup..crclbar. M.sup..sym.).sub.2, where L is C.sub.1 -C.sub.4 -alkylene and M.sup..sym. has the abovementioned meaning, and may be interrupted by from 1 to 4 ether oxygen atoms, from 1 to 4 imino or C.sub.1 -C.sub.4 -alkylimino groups or a radical of the formula N--CH.sub.2 --COO.sup..crclbar. M.sup..sym., where M.sup..sym. has the abovementioned meaning, or is phenyl which is unsubstituted or substituted by carboxyl, with the proviso that, when R is alkyl which has one or more hetero atoms, at least 5 carbon atoms bonded to one another are present in R, and the use of the above-mentioned compounds as charge stabilizers in electrostatic toners.
Latent electrostatic image recordings are developed by inductively recording the toner on the electrostatic image. The charge stabilizers stabilize the electrostatic charge of the toner. This makes the image stronger and gives it crisper contours.
The charge stabilizers used must meet a wide range of requirements:
ability to develop the latent electrostatic image into a visible image having high color strength
capability of being readily distributed in the toner formulation in order to produce a faultless, uniform image having crisp contours
insensitivity to moisture
high heat stability.
EP-A-132 718 discloses electrostatic toners which contain N-acylated 3-aminopropionic acid derivatives as charge stabilizers.
Furthermore, U.S. Pat. No. 3,974,496 discloses photosensitive photographic materials which contain, as photosensitive material, silver salts of aminodiacetic acid and specific derivatives thereof.
However, it has been found that the prior art charge stabilizers frequently do not meet all requirements.
It is an object of the present invention to provide novel electrostatic toners which have charge stabilizers which possess advantageous performance characteristics.
We have found that this object is achieved by the electrostatic toners defined at the outset and containing aminodiacetic acid derivatives of the formula I as charge stabilizers.
All alkyl and alkylene groups occurring in the abovementioned formula I may be both straight-chain and branched.
If substituted phenyl groups occur in the above-mentioned formula I, they have, as a rule, from 1 to 3 substituents.
R is, for example, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, 2-methylpentyl, heptyl, octyl, 2-ethylhexyl, isooctyl, nonyl, isononyl, decyl, isodecyl, undecyl, dodecyl, tridecyl, 3,5,5,7-tetramethylnonyl, isotridecyl (the above names isooctyl, isononyl, isodecyl and isotridecyl are trivial names and originate from the alcohols obtained by the oxo synthesis; cf. Ullmanns Enzyklopadie der technischen Chemie, 4th Edition, Volume 7, pages 215 to 217, and Volume 11, pages 435 and 436), tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, eicosyl, heneicosyl, 1-carboxyethyl, 1-carboxypropyl, 1-carboxybutyl, benzyl, 1- or 2-phenylethyl, 2-hydroxybenzyl, 3,5-dimethylbenzyl, 3,5-dibutylbenzyl, 3,5-di-tert-butylbenzyl, 2-hydroxy-3,5-di-tert-butylbenzyl, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2- or 3-methoxypropyl, 2- or 3-ethoxypropyl, 2- or 3-propoxypropyl, 2- or 3-butoxypropyl, 2- or 4-methoxybutyl, 2- or 4-ethoxybutyl, 2- or 4-propoxybutyl, 2- or 4-butoxybutyl, 3,6-dioxaheptyl, 3,6-dioxaoctyl, 4,8-dioxanonyl, 3,7-dioxaoctyl, 3,7-dioxanonyl, 4,7-dioxaoctyl, 4,7-dioxanonyl, 4,8-dioxadecyl, 3,6,8-trioxadecyl, 3,6,9-trioxaundecyl, 3,6,9,12-tetraoxatridecyl, 3,6,9,12-tetraoxatetradecyl, 2-mono- or dimethylaminoethyl, 2-mono- or diethylaminoethyl, 2- or 3-mono or dimethylam

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