Radiation imagery chemistry: process – composition – or product th – Electric or magnetic imagery – e.g. – xerography,... – Post imaging process – finishing – or perfecting composition...
Reexamination Certificate
2001-11-20
2003-03-04
Dote, Janis L. (Department: 1756)
Radiation imagery chemistry: process, composition, or product th
Electric or magnetic imagery, e.g., xerography,...
Post imaging process, finishing, or perfecting composition...
C430S137140, C524S083000
Reexamination Certificate
active
06528223
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to electrostatographic toners and, more particularly, to a composition for forming magenta-colored toner particles and to toner particles formed therefrom.
BACKGROUND OF THE INVENTION
When Neptune 525, a magenta-colored dye commercially available from BASF, is employed in an evaporative limited coalescence (ELC) process, dye crystallization occurs during the evaporation of the ethyl acetate used in the process, resulting in the formation of a substantial number of toner particles containing little or no dye.
It is generally recognized that crystallization rates are enhanced by factors such as molecular symmetry and coplanarity that allow for the close packing and alignment of molecules. To eliminate or substantially reduce the tendency towards crystallization exhibited by dyes such as Neptune 525, one might consider variations in dye molecular structure that would hinder molecular packing.
International Patent Application WO 92/19684 and the corresponding Canadian Patent Application No. 2106779, issued to BASF AG, describe N-aminopyridone dyes of formula (I), wherein R
1
represents hydrogen or C
1
-C
4
alkyl, R
2
and R
3
may be identical or different and independently represent hydrogen, optionally substituted C
1
-C
12
alkyl, C
5
-C
7
cycloalkyl, optionally substituted phenyl, optionally substituted pyridyl, optionally substituted C
1
-C
12
alkanoyl, C
1
-C
12
alkoxycarbonyl, optionally substituted C
1
-C
12
cycloalkylsulphonyl, optionally substituted phenyl substituted phenylsulphonyl, pyridylsulphonyl, optionally substituted benzoyl, pyridylcarbonyl, or thienylcarbonyl, or R
2
and R
3
together with the nitrogen atom linking them represent succinimido optionally substituted by C
1
-C
4
alkyl, phthalimido optionally substituted by C
1
-C
4
alkyl, or a five- or six-membered saturated heterocylic residue optionally containing additional heteroatoms, and X represents CH or nitrogen, Y represents cyano or a residue of formula CO—W, CO—OW or CO—NHW, wherein W represents hydrogen, C
1
-C
8
alkyl that is optionally substituted and may be interrupted by one or two oxygen atoms with an ether function, C
5
-C
7
cycloalkyl, phenyl, or tolyl, and Z represents an aromatic carbocyclic or heterocyclic residue.
The applications further disclose a process for transferring a pyridone dye from a transfer to plastic-coated paper by diffusion or sublimation with the aid of an energy source.
SUMMARY OF THE INVENTION
The present invention is directed to composition for electrostatographic toner particles that comprises an organic binder polymer and a dye having the structure
wherein R
1
represents hydrogen or an alkyl group containing 1 to about 4 carbon atoms, R
2
and R
3
each individually represents hydrogen, a substituted or unsubstituted alkyl group containing 1 to about 12 carbon atoms, a cycloalkyl group containing 5 to 7 carbon atoms, a substituted or unsubstituted phenyl group, a substituted or unsubstituted pyridyl group, an alkanoyl group containing 2 to about 12 carbon atoms, an alkoxycarbonyl group containing 2 to about 12 carbon atoms, an alkylsulfonyl group containing 1 to about 12 carbon atoms, a cycloalkylsulfonyl group containing 5 to 7 carbon atoms, a substituted or unsubstituted phenylsulfonyl group, a substituted or unsubstituted pyridylsulfonyl group, a substituted or unsubstituted benzoyl group, a substituted or unsubstituted pyridylcarbonyl group, or a substituted or unsubstituted thienylcarbonyl group; or R
2
and R
3
together with the nitrogen atom represents a substituted or unsubstituted succinimido group, a substituted or unsubstituted phthalimido group, or a 5- or 6-membered saturated heterocyclic group; Y represents cyano or a residue of formula CO—W, CO—OW or CO—NHW, wherein W represents hydrogen, a substituted or unsubstituted alkyl group containing 1 to about 8 carbon atoms, an alkoxyalkyl group containing up to about 8 carbon atoms, a cycloalkyl group containing 5 to 7 carbon atoms, a substituted or unsubstituted phenyl group; and Z represents a thiazole moiety II
wherein R
4
and R
5
each individually represents a substituted or unsubstituted alkyl group containing 1 to about 8 carbon atoms, or R
4
and R
5
taken together with N represent a 5- or 6-membered cyclic ring system, and R
6
represents a substituted or unsubstituted alkyl, aryl, alkenyl, or cycloalkyl group containing up to about 10 carbon atoms.
DETAILED DESCRIPTION OF THE INVENTION
In structure I above, R
1
preferably represents a methyl group, R
2
preferably represents hydrogen, R
3
preferably represents a benzoyl group, and Y preferably represents a cyano group.
In structure II above, R
4
and R
5
can represent the same alkyl group, preferably an n-butyl group. R
4
and R
5
together with N can also represent a morpholino group, a piperidino group, or a pyrrolidino group. R
6
preferably represents an alkyl group, more preferably, a methyl group.
Synthesis Scheme 1 below, a modification of that described in WO 92/19684, was utilized in the preparation of the thiazole N-aminopyridone dyes of the present invention In Scheme 1 as well as in Schemes 2, 3, and 4 that follow, Ar represents, in accordance with the present invention, a phenyl ring substituted at the 3-position with a substituted or unsubstituted alkoxy, alkenoxy, cycloalkoxy, or aryloxy group containing up to about 10 carbon atoms. Preferably, the phenyl 3-substituent is an unsubstituted alkoxy group, more preferably, a methoxy group.
As shown in Scheme 1, the first step is the reaction of an aroyl chloride with potassium thiocyanate, followed by reaction of the resulting product with a secondary amine to form the corresponding thiourea, using the general procedure included in Example 1 of U.S. Pat. No. 4,560,751. The structures of thioureas so prepared are presented in Table 1.
The second step of the synthesis sequence, Scheme 2 below, utilizes the general procedure of Example 1 of U.S. Pat. No. 4,560,751 for the reaction of the thioureas with chloroacetic acid to give the 2-amino-4-arylthiazoles. The structure of the 2-amino-4-arylthiazoles prepared are shown in Table 2.
The third step of the reaction sequence, Scheme 3 below, entails formylation of the 2-amino-4-arylthiazoles at the 5-position via the Vilsmeier reaction from phosphorous oxychloride and DMF, following the general procedure reported in
J. Chem. Soc., Perkin Trans. I,
1983, p.346. The structures of the thiazole aldehydes prepared are shown in Table 3.
The next step of the reaction sequence, Scheme 4 below, is the acylation of 1-amino-5-cyano-2-hydroxy-4-methyl-6-pyridone, prepared as reported in
Polish Journal of Chemistry,
Vol. 58, 1984, page 85 (CA 123:313975), followed by condensation of the acylated product with a thiazole aldehyde. The general procedure described in WO 92/19684 was used to prepare the pyridone dyes, whose structures are shown in Table 4.
Acylamino-5-cyano-2-hydroxy4-methyl-6-pyridones, in particular, the benzoylamino derivative, can be also prepared by Scheme 5, shown below.
Although not wishing to be bounds by the following interpretation, it is possible that an aromatic substituent such as the phenyl group at the 4-position of the thiazole ring shown in structure III below resides in an extended conjugated coplanar arrangement with the thiazole nucleus. Such an arrangement might be expected to facilitate alignment of molecules in such a way as to result in crystallization of the dye. To avoid this possible tendency towards dye crystallization, various substituents were introduced into the aromatic ring at the thiazolyl 4-position. Substitution of a 3-methoxy group of the phenyl ring, as shown in structure IV below, yielded a dye that did not crystallize when subjected to an evaporative limited coalescence process. Furthermore when this dye was used to make toner particles, all of the particles were colored. It is theorized that a combination of steric effects and hydrogen bonding resulting from the introduction of the 3-methoxy substituent into the phenyl grou
Ezenyilimba Matthew C
Tyagi Dinesh
Wilson John C
Dote Janis L.
NexPress Solutions LLC
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