Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Post imaging process – finishing – or perfecting composition...
Patent
1997-05-05
1999-03-16
Goodrow, John
Radiation imagery chemistry: process, composition, or product th
Electric or magnetic imagery, e.g., xerography,...
Post imaging process, finishing, or perfecting composition...
G03G 9097
Patent
active
058828338
DESCRIPTION:
BRIEF SUMMARY
This application is the national phase of international application PCT/GB95/02432, filed Oct. 16, 1995 which was designated the U.S.
The present invention relates to compositions comprising a toner resin and a guanidine salt of an aromatic sulphonic acid (hereinafter "GAS"), and the use of such salts as a positive charge control agent (hereinafter "CCA"). Some of the salts are novel.
EP 178,952 discloses a composition comprising a base material and a guanidine and its use as a positive CCA in electroreprographic imaging processes.
It has now been found that an aromatic sulphonic acid salt of a guanidine exhibits superior properties as CCA when compared with the guanidine itself especially with respect to superior compatibility with the toner resin, higher tribo-electric charge and reduced usage of the guanidine.
According to the present invention there is provided a toner resin composition comprising a toner resin and an aromatic sulphonic acid salt of a guanidine of Formula 1 ##STR1## wherein R.sup.1 to R.sup.5 are the same or different and are hydrogen, C.sub.1-18 -optionally substituted alkyl, C.sub.1-10 -optionally substituted cycloalkyl, C.sub.1-18 -alkenyl, aralkyl, optionally substituted aryl or heterocyclyl or R.sup.1 and R.sup.2 together with the nitrogen atom to which they are attached and/or R.sup.3 and R.sup.4 together with the nitrogen atom to which they are attached, form a 6-membered ring and where at least one of the groups R.sup.1 to R.sup.5 is other than H.
When R.sup.1 to R.sup.5 is alkyl or substituted alkyl, the alkyl chain may be linear or branched, but is preferably linear. It is also preferably C.sub.1-12 - and especially C.sub.1-6 -alkyl.
When the alkyl group is substituted, the substituent or substituents are hydroxy, amino, substituted amino, halogen or nitrile.
Preferably, the alkyl group is unsubstituted.
When R.sup.1 to R.sup.5 is cycloalkyl, it is preferably C.sub.3-6 -cycloalkyl and especially cyclohexyl.
Any substituent present in the cycloalkyl group is preferably C.sub.1-4 -alkyl or C.sub.1-4 -alkoxy, but it is preferred that the cycloalkyl group is unsubstituted.
When R.sup.1 to R.sup.5 is alkenyl it is preferably C.sub.1-10 -, more preferably C.sub.1-6 - and especially C.sub.1-4 -alkenyl such as propen-2-yl.
When R.sup.1 to R.sup.5 is aryl it is preferably phenyl or naphthyl which may be substituted by one or more C.sub.1-6 -alkyl, C.sub.1-6 -alkoxy, halogen, nitro or nitrile groups. When present, the substituent is preferably in the 2 and/or 4-position.
When R.sup.1 to R.sup.5 is heterocyclic, the heterocyclic ring preferably contains 5- or 6-members as in a pyridyl, furanyl or thienyl ring.
When R.sup.1 and R.sup.2 and/or R.sup.3 and R.sup.4 together with the nitrogen atom to which they are attached form a 6-membered ring it is preferably morpholino, piperidino, piperazino or N-(C.sub.1-6 -alkyl)piperazino.
In the foregoing, halogen means fluorine, bromine, iodine and especially chlorine.
One preferred class of guanidine is where R.sup.1 and R.sup.3 are the same and R.sup.2 and R.sup.4 are the same. A particularly preferred class of compound is where R.sup.1 and R.sup.3 are both hydrogen and R.sup.2 and R.sup.4 are independently optionally substituted aryl and in an especially preferred class of guanidines, R.sup.5 is hydrogen.
Examples of guanidines are diphenylguanidine, triphenylguanidine, tri-1-naphthylguanidine, N,N.sup.1 -di(4-methyl phenyl) guanidine, N,N'-di(2-methylphenyl)guanidine and N,N.sup.1 -di(2-methyl-4-ethylphenyl)guanidine.
Good results have been obtained with diphenylguanidine and N,N'-di(2-methylphenyl)guanidine.
The aromatic sulphonic acid (hereinafter "ASA") is preferably carbocyclic and is more preferably a derivative of benzene and especially a derivative of naphthalene. The ASA may contain more than one sulphonic acid group. Preferred ASA's contain two sulphonic acid groups.
The ASA may also contain other substituents such as hydroxy, amino, substituted amino, halogen, nitro or carboxy. Halogen is as hereinbefore defined.
When the ASA contain
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patent: 3776757 (1973-12-01), Eastman et al.
patent: 4663263 (1987-05-01), Ikeda et al.
Rasmussen et al: Synthesis, No. 6, 1988, pp. 460-466, see p. 464, entry 51.
Lamattina et al: Journal of Medicinal Chemistry, vol. 33, No. 2, 1990, pp. 643-552, see p. 548; table V see p. 550, compound 130.
Schwobel et al: Liebigs Annalen Der Chemie, 1984, pp. 900-903, see p. 903.
Patent Abstracts of Japan, vol. 10, No. 278 (P-499), Sep. 20, 1986, & JP,A,61 099153 (Canon), May 17, 1986, see abstract.
Patent Abstracts of Japan, vol. 11, No. 112 (P-565), Apr. 9, 1987, & JP,A,61 260255 (Canon) Nov. 18, 1986, see abstract.
Goodrow John
Zeneca Limited
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