Aromatic bis-acetoacetamide intermediates

Details Aromatic bis-acetoacetamide intermediates Aromatic bis-acetoacetamide intermediates

2001-11-21

2002-12-31

Powers, Flona T. (Department: 1626)

Organic compounds -- part of the class 532-570 series

Organic compounds

Azo

C564S154000, C564S155000

Reexamination Certificate

active

06500935

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to specific novel compounds of aromatic bis-acetoamide structures. Such compounds are useful as intermediates in the production of certain bis-acetoanilide azo dyes, pigments, and polymeric colorants. Such compounds facilitate production of such coloring agents that exhibit favorable tinctorial strength and intense color from orange to greenish yellow within and on different substrates and media. Coloring agents and methods of making such agents are encompassed within this invention as well.
DISCUSSION OF THE PRIOR ART
All U.S. patents cited within this specification are hereby incorporated by reference.
Bis-acetoacetanilide azo yellow and orange pigments, dyes, and dyestuffs are well known and are commonly used in various types of printing inks. They also generally provide effective coloration to certain substrates, such as plastics, paints, textiles, and the like. Such coloring agents provide acceptable colorations; however, the versatility of such coloring agents within and on different media and substrates has been rather limited. Such limits have been noticeable due to a limit on the number and types of different bis-acetoacetanilide coloring agents available from the low number of known and utilized bis-acetoacetamide intermediates within the industry. Furthermore, such coloring agents have exhibited toxicity problems primarily due to the specific bridging groups between the two acetoacetamide moieties of such traditional intermediates. Such toxicity issues are basically related to the decomposition by-products of traditional bis-acetoacetanilide, and the like, coloring agents, particularly in plastic applications, and are rising concerns to consumers. For example, Pigment Yellow 17 (structure below) is a strong greenish-shade bis-acetoacetanilide yellow and has often been incorporated within plastics.
However, as reported by R. Az et al in
Dyes and pigments,
15, 1 (1991), such a coloring agent degrades into potentially carcinogenic by-products (e.g. 3,3′-dichlorobenzidine) in plastics processed above 200° C., a temperature lower than that used in processing most plastics (e.g., from about 230° C. to about 330° C.). In efforts to overcome these disadvantages, azo pigment manufacturers have actively pursued development of other types of bis-acetoacetanilinde colors by using various intermediates.
Alternative pigments have been developed by coupling diacetoacet-1,4-phenylenediamide with aniline derivatives. For example, U.S. Pat. No. 5,616,778 discloses coupling diacetoacet- 1,4-phenylenediamide with 2,5-dicarbomethoxyaniline to produce Pigment Yellow 155 (structure below). As another example, U.S. Pat. No. 5,559,216 discloses 47 different examples of coupling diacetoacet-1,4-phenylenediamide with various aniline derivatives and describes the related processes for making such bis-acetoacetanilide pigments. Other examples of such alternatives include the following patents: German Patent 3,501,199, Canadian Patent 1,135,688, and U.S. Pat. Nos. 5,889,162, 4,146,558, and 4,103,092.
Very few reports exist in the pertinent literature regarding the coupling of such alternative bis-acetoacetamide starting materials with 4,4′-bi-o-acetoacetotoluidine (Naphthol AS-G) into anilines to another type of Bis-AAA colorants. U.S. Pat. Nos. 4,146,558 and 4,206,144 describe a process to make a water-soluble bright yellow dyestuff having the formula
Such biphenyl bridged coloring agents, however, exhibit toxicity which limits its use to certain products.
As noted above, there is still a noticeable need to develop new intermediates to synthesize new bis-acetoanilide azo coloring agents, to meet various coloration needs in diversified commercial market requirements, such as toxicity, brightness, strength and the like. Hence, there still exists a need to develop a method, and well as possible intermediate compounds, which facilitate production of such bis-acetoanilide azo coloring agents.
DESCRIPTION OF THE INVENTION
It is thus an object of the invention to provide a novel method of producing such desirable bis-acetoacetanilide coloring agents through the reaction of a novel bis-acetoacetamide intermediate with any number of amine groups. Another object of this invention is to provide a novel bis-acetoacetamide intermediate compound.
It is to be understood that the term alkyl as used throughout is intended to encompass any straight or branched alkyl moiety, having anywhere from 1 to 30 carbons therein; the same chain length applies to the term “alkoxy” as well. Also, the term substitued phenyl is intended to encompass any phenyl system having any type of pendant group attached thereto, including, without limitation, alkyl groups, alkylene groups, alcohol groups, ether groups, ester groups, amine groups, amide groups, hydroxyls, and the like. Phenyl is basically an unsubstituted ring system (and thus includes hydrogens only).
The present invention preferably encompasses the utilization of and the compound of Formula (I)
wherein R is alkyl, phenyl, polyphenyl, or substituted phenyl; E is H, halogen, alkyl, alkoxy, or phenyl; and a is 1 or 2, wherein if a is 1, then A is O, SO
2
N, methylene, S, N(R′) or a moiety of Structure (II)
wherein R′ is alkyl or hydrogen, and if a is 2, then A is O, SO
2
, methylene, S, N(R′), wherein R′ is alkyl or hydrogen.
Such an intermediate is thus utilized as a reactant with any number of amine-containing compounds to form bis-acetoacetanilide azo coloring agents. It is intended that the term “coloring agent” encompasses any color-producing or -exhibiting compound including, without limitation, dyes, pigments, polymeric colorants, dyestuffs, and the like. Basically, any bis-acetoacetanilide color-producing or -exhibiting compound falls within such definition.
In order to produce such coloring agents, the aforementioned novel intermediate must be reacted with an amine, particularly in a 1:2 molar ratio to produce the necessary two azo groups to provide the desired colorations. To produce a bis-acetoacetanilide pigment, dye, or dyestuff, the inventive intermediate is reacted with any number of aniline derivatives. The production of a pigment or dye is dependent primarily upon the types of pendant groups present on such aniline derivatives. Other amine compounds may be utilized as reactants as long as azo groups result from such reaction and thus produces a coloring agent. Also, the molar ratio of the intermediate in relation to amine may be anywhere from about 1:0.1 to about 1:3, depending on the degree of azotization desired. Preferably, again, this ratio is 1:2 intermediate to amine.
DESCRIPTION OF THE PREFERRED EMBODIMENT
The specific formulations below, as well as the following exemplified methods of producing such and methods of coloring using such are thus indicative of the preferred embodiments of this invention:
Intermediate Formation


REFERENCES:
patent: 4103092 (1978-07-01), Jefferies et al.
patent: 4146558 (1979-03-01), Jefferies et al.
patent: 4206144 (1980-06-01), Jefferies et al.
patent: 4754021 (1988-06-01), Mockli
patent: 5559216 (1996-09-01), Jung et al.
patent: 5616778 (1997-04-01), Goldmann et al.
patent: 5889162 (1999-03-01), Hays
patent: 26 33 292 (1976-07-01), None
patent: 35 01 199 (1985-01-01), None
patent: 45-000069 (1970-01-01), None
Chemical Abstracts, 73:57132, 1970.*
Moeckli, Chemical Abstracts, 106:6405, 1987.*
Kleine et al., Chemical Abstracts, 188:214883, 1993.*
Shibata et al., Chemical Abstracts, 118:222798, 1993.*
Yamada et al., Chemical Abstracts, 72:134132, 1970.*
Zhenyi et al., Dyes and Pigments, 1994, 25(3), 241-248.

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