Organic compounds -- part of the class 532-570 series – Organic compounds – Azo
Reexamination Certificate
2002-06-27
2003-06-10
Powers, Fiona T. (Department: 1626)
Organic compounds -- part of the class 532-570 series
Organic compounds
Azo
C534S757000, C534SDIG002, C560S049000
Reexamination Certificate
active
06576747
ABSTRACT:
BACKGROUND OF THE INVENTION
The present invention is directed to a process for preparing dianthranilate compounds. More specifically, the present invention is directed to a process for preparing dianthranilate compounds containing relatively large hydrocarbon moieties, and to processes for preparing diazopyridone colorants with these dianthranilate compounds. One embodiment of the present invention is directed to a process for preparing dianthranilate compounds which comprises (a) admixing (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
Another embodiment of the present invention is directed to a process for preparing a diazopyridone colorant which comprises (I) preparing a dianthranilate compound by (a) admixing (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 dial, and (4) a solvent; and (b) heating the mixture thus formed to form a dianthranilate compound of the formula
(II) reacting the dianthranilate compound with nitrosylsulfuric acid to form a diazonium salt of the formula
and (III) reacting the diazonium salt with a pyridone compound of the formula
wherein R
2
is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, (iv) an alkylaryl group, (v) an alkoxy group, (vi) an aryloxy group, (vii) an arylalkyloxy group, (viii) an alkylaryloxy group, (ix) a polyalkyleneoxy group, (x) a polyaryleneoxy group, (xi) a polyarylalkyleneoxy group, (xii) a polyalkylaryleneoxy group, (xiii) a heterocyclic group, (xiv) a silyl group, (xv) a siloxane group, (xvi) a polysilylene group, (xvii) a polysiloxane group, or (xviii) a group of the formula
wherein r and s are each, independently of the other, integers representing a number of repeat —CH
2
— groups, and R
3
is (i) an alkyl group, (ii) an aryl group, (iii) an arylalkyl group, or (iv) an alkylaryl group, to form a diazopyridone compound of the formula
Methods for the preparation of simple anthranilate esters with isatoic anhydride and simple alcohols are known. These methods, however, when used to attempt to prepare anthranilate compounds from diols of relatively large hydrocarbons, exhibit disadvantages such as low yield and the production of undesirable intermediate products and byproducts. Moreover, known syntheses of dianthranilates have the added complication of entailing two consecutive additions of an intermediate, isatoic anhydride, to a diol, which can lead to contamination by a monoanthranilate mono alcohol if the reaction is not forced to completion. This monoanthranilate can be difficult to remove from the dianthranilate. Dianthranilates containing relatively large hydrocarbon moieties can be used to prepare specific diazopyridone colorants.
U.S. Pat. No. 3,929,863 (Blahak et al.) and German Patent Publication DE 2 040 644, the disclosures of each of which are totally incorporated herein by reference, disclose aromatic diamines having the general formula
wherein n is an integer of from 2 to 8, X is sulfur or oxygen, and R is an n-valent hydrocarbon radical which may be interrupted by O or S atoms and which is obtained by removing OH or SH groups from a polyol or polythiol having a molecular weight of less than 600 which are prepared by reacting a compound having the formula (HX)
n
R where X, n, and R as defined above with about n-equivalents of an isatoic acid anhydride in the presence of a strong base. The aromatic diamines of the invention are particularly useful as the active hydrogen containing component for reaction with polyisocyanates in the preparation of synthetic resins by the isocyanate-polyaddition process.
German Patent Publication DE 2 902 740 and European Patent Publication EP 0 013 956, the disclosures of each of which are totally incorporated herein by reference, disclose a process for the preparation of bis-(aminobenzoic acid)-alkanediol diester by esterification of alkanediols, except those in which hydroxy groups are in 1.4 or 2.5-positions, which nitrobenzoic acids and subsequent catalytic reduction of the bis-(nitrobenzoic acid)-alkanediol diester compound in a polar organic solvent, this solvent being partly or homogeneously miscible with water in all proportions, characterized by that the esterification is carried out in the presence of an aromatic sulfonic acid as a catalyst and in the absence of a solvent and at a temperature between 150 and 175° C.
“Polyamines Containing Ester Groups as Structural Components in Polyurethane Chemistry, J. Blahak et al., Angew. Makromol. Chem. (1972), Vol. 26, pp. 29 to 45, the disclosure of which is totally incorporated herein by reference, discloses aromatic diamines containing ester groups, such as 4-chloro-3,5-diaminobenzoates and aminophenyl aminobenzoates, which were prepared and used as noncarcinogenic and nontoxic chain extenders for polyurethane elastomers, giving processing and mechanical properties similar to those obtained with 3,3′-dichloro-4,4′-diaminodiphenylmethane. Anthranilates of both high and low molecular weight polyols were also used, but were much less reactive than compounds with amino groups in the meta or para position.
“The Chemistry of Isatoic Anhydride,” G. M. Coppola,
Synthesis
, p. 505 (1980), the disclosure of which is totally incorporated herein by reference, discloses various reactions to synthesize isatoic anhydride and reactions of isatoic anhydride with various classes of compounds, including alcohols.
“Isatoic Anhydride. IV. Reactions with Various Nucleophiles,” R. P. Staiger et al.,
J. Org. Chem
., Vol. 24, p. 1214 (1959), the disclosure of which is totally incorporated herein by reference, discloses reactions of isatoic anhydride with alcohols, mercaptans, and compounds with active methylene groups forming substituted esters, thio esters, carbamates, and substituted quinolines. A mechanism for the alternate cleavage of the anhydride ring is elucidated.
European Patent Publication 1 125 990 and PCT Patent Publication WO 01/09256, the disclosures of each of which are totally incorporated herein by reference, discloses an aqueous ink for ink jet recording which contains at least a water-insoluble coloring matter, water, and a resin as main components and which takes the form of an emulsion, which is characterized by containing at least one yellow hue coloring matter selected from the group consisting of a quinophthalone compound represented by the formula (1)
wherein each of R
1
to R
3
independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, —CONR
4
R
5
, or —COOR
6
(in which each of R
4
to R
6
independently represents a hydrogen atom, an unsubstituted or substituted alkyl group, or an unsubstituted or substituted aryl group) and all of R
1
to R
3
are not a hydrogen atom at the same time, and a pyridone azo compound represented by the formula (2)
wherein each of R
7
to R
11
independently represents a hydrogen atom, a halogen atom, an unsubstituted or substituted alkyl group, an aralkyl group, an unsubstituted or substituted alkoxy group, an unsubstituted or substituted aryl group, an unsubstituted or substitut
Banning Jeffrey H.
Carlini Rina
Duff James M.
Gaynor Roger E.
Liebermann George
Byorick Judith L.
Powers Fiona T.
Xerox Corporation
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