Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2002-06-27
2003-11-11
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S651000, C534S758000, C534SDIG002
Reexamination Certificate
active
06646111
ABSTRACT:
Cross-reference is made to the following applications:
Copending application U.S. Serial No. 10/185,261, filed concurrently herewith, entitled “Processes for Preparing Dianthranilate Compounds and Diazopyridone Colorants,” with the named inventors Rina Carlini, James M. Duff, Stephen G. Robinson, George Liebermann, Roger E. Gaynor, Tania L. Pereira, Jeffery H. Banning, and James D. Mayo, the disclosure of which is totally incorporated herein by reference, discloses a process for preparing dianthranilate compounds which comprises (a) admixing reactants as follows: (1) a diol of the formula R
1
(OH)
2
, wherein R
1
is an alkylene group having at least about 20 carbon atoms, and wherein the —OH groups are primary or secondary, (2) isatoic anhydride, present in an amount of at least about 2 moles of isatoic anhydride per every one mole of diol, (3) a catalyst which is 1,4-diazabicyclo[2.2.2]octane, N,N,N′,N′-tetramethylethylene diamine, or a mixture thereof, said catalyst being present in an amount of at least about 0.2 mole of catalyst per every one mole of diol, and (4) a solvent; and (b) heating the mixture thus formed to form a dianthranilate compound of the formula
Also disclosed is a process for preparing diazopyridone colorants which comprises (I) preparing a dianthranilate compound by the aforementioned method, (II) reacting the dianthranilate compound with nitrosylsulfuric acid to form a diazonium salt, and (III) reacting the diazonium salt with a pyridone compound to form a diazopyridone compound.
Copending application U.S. Serial No. 10/185,994, filed concurrently herewith, entitled “Dimeric Azo Pyridone Colorants,” with the named inventors Rina Carlini, Jeffery H. Banning, James M. Duff, Bo Wu, and James D. Mayo, the disclosure of which is totally incorporated herein by reference, discloses compounds of the formula
The compounds are useful as colorants, particularly in applications such as phase change inks.
Copending application U.S. Serial No. 10/184,269, filed concurrently herewith, entitled “Phase Change Inks Containing Dimeric Azo Pyridone Colorants,” with the named inventors Bo Wu, Rina Carlini, Jeffery H. Banning, James M. Duff, James D. Mayo, Jule W. Thomas, Paul F. Smith, and Michael B. Meinhardt, the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula
Copending application U.S. Serial No. 10/185,264, filed concurrently herewith, entitled “Phase Change Inks Containing Azo Pyridone Colorants” with the named inventors Jeffery H. Banning, Bo Wu, James D. Mayo, James M. Duff, Rina Carlini, Jule W. Thomas, and Paul F. Smith, the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula
Copending application U.S. Serial No. 10/186,024, filed concurrently herewith, entitled “Azo Pyridone Colorants,” with the named inventors Jeffery H. Banning, Rina Carlini, James D. Mayo, James M. Duff, and C. Wayne Jaeger, the disclosure of which is totally incorporated herein by reference, discloses compounds of the formula
The compounds are useful as colorants, particularly in applications such as phase change inks.
Copending application U.S. Serial No. 10/185,597, filed concurrently herewith, entitled “Process for Preparing Substituted Pyridone Compounds,” with the named inventors James D. Mayo, James M. Duff, Rina Carlini, Roger E. Gaynor, and George Liebermann, the disclosure of which is totally incorporated herein by reference, discloses a process for preparing substituted pyridone compounds which comprises (a) admixing in the absence of a solvent (1) an amine of the formula R
1
—NH
2
wherein R
1
is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, and (2) a first ester of the formula
wherein R
2
is an electron withdrawing group and R
3
is an alkyl group; (b) heating the mixture containing the amine and the first ester to form an intermediate compound of the formula
(c) admixing the intermediate compound with (1) a base and (2) a second ester of the formula
wherein R
4
is an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group and R
5
is an alkyl group, said second ester being present in a molar excess relative to the intermediate compound, said base being present in a molar excess relative to the intermediate compound, and (d) heating the mixture containing the intermediate compound, the second ester, and the base to form a pyridone compound of the formula
or a salt thereof. Also disclosed is a process for preparing diazopyridone colorants which comprises preparing a pyridone compound by the above process and reacting the pyridone compound with a diazonium salt to form a diazopyridone compound.
Copending application U.S. Serial No. 10/185,828, filed concurrently herewith, entitled “Method for Making Dimeric Azo Pyridone Colorants,” with the named inventors Rina Carlini, James D. Mayo, James M. Duff, Jeffery H. Banning, Paul F. Smith, George Liebermann, and Roger E. Gaynor, the disclosure of which is totally incorporated herein by reference, discloses a process for preparing a diazopyridone compound which comprises (a) preparing a first solution comprising (1) either (A) a dianiline of the formula
or (B) an aniline of the formula
and (2) a first solvent mixture comprising (I) a solvent, (II) acetic acid, and (III) an optional second acid, said acetic acid being present in the solvent mixture in an amount of at least about 95 percent by weight of the solvent mixture, said first solution being at a temperature of about +15° C. or lower; (b) adding to the first solution nitrosylsulfuric acid, thereby forming a diazonium salt either (A) of the formula
or (B) of the formula
(c) preparing a second solution comprising (1) a second solvent mixture comprising water and an organic solvent soluble in or miscible in water, (2) either (A) a pyridone of the formula
or (B) a dipyridone of the formula
(3) a base present in an amount of at least about 3 molar equivalents of base per mole of pyridone moiety, and (4) an optional buffer salt, and (d) combining either (A) the second solution containing the dianiline and the first solution containing the pyridone, or (B) the second solution containing the aniline and the first solution containing the dipyridone to form a third solution and effect a coupling reaction to form a diazopyridone compound either (A) of the formula
or (B) of the formula
Copending application U.S. Serial No. 10/184,266, filed concurrently herewith, entitled “Phase Change Inks Containing Dimeric Azo Pyridone Colorants,” with the named inventors Bo Wu, Rina Carlini, James M. Duff, Jeffery H. Banning, and James D. Mayo, the disclosure of which is totally incorporated herein by reference, discloses a phase change ink composition comprising a phase change ink carrier and a colorant compound of the formula
BACKGROUND OF THE INVENTION
The present invention is directed to colorant compounds. More specifically, the present invention is directed to dimeric azo pyridone colorant compounds particularly suitable for use in hot melt or phase change inks. One embodiment of the present invention is directed to compounds of the formula
wherein (A) X and X′ each, independently of the other, is (i) a direct bond, (ii) an oxygen atom, (iii) a sulfur atom, (iv) a group of the formula —NR
40
— wherein R
40
is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, or (v) a group of the formula —CR
50
R
60
— wherein R
50
and R
60
each, independently of the other, is a hydrogen atom, an alkyl group, an aryl group, an arylalkyl group, or an alkylaryl group, (B) Z and Z′ each, independently of the other, is (i) a hydrogen atom, (ii) a halogen atom, (iii) a nitro group, (iv) an alkyl group, (v) an aryl group, (vi) an arylalkyl group, (vii) an alkylaryl group, (viii) a group of the formula
wherein R
70
is
Banning Jeffrey H.
Carlini Rina
Duff James M.
Mayo James D.
Wu Bo
Byorick Judith L.
Powers Fiona T.
Xerox Corporation
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