Polymeric bis-acetoacetanilide azo colorants

Details Polymeric bis-acetoacetanilide azo colorants Polymeric bis-acetoacetanilide azo colorants

2001-11-21

2002-11-12

Powers, Fiona T. (Department: 1626)

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

Organic compounds

Azo

C534S745000, C524S190000

Reexamination Certificate

active

06479648

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to colorants comprising a chromophore having two azo acetoacetanilide moieties, wherein said moieties each have at least one poly(oxyalkylene) chain, preferably at least two such chains. Such colorants exhibit excellent good base stability and lightfastness, particularly when incorporated within certain media and/or on the surface of certain substrates. These poly(oxyalkylene) chains provide solubility in different solvents or resins thereby permitting the introduction of such excellent coloring chromophores within diverse media and/or or diverse substrates. Compositions and articles comprising such colorants are provided as are methods for producing such inventive colorants.
DISCUSSION OF THE PRIOR ART
All U.S. patents cited within this specification are hereby incorporated by reference.
Bis-acetoacetanilide azo pigments, dyes, and dyestuffs generally provide effective and desirable colorations to certain substrates, such as textiles, paper, and the like. However, their use is limited to such a narrow range of substrates and/or media due to the difficulty of solubility, comparability, and migratory problems inherent with such pigments, dyes, or dyestuffs. Such pigments, dyes, and/or dyestuffs have not been widely introduced as colorants within plastics (such as polyolefins, polyurethanes, and the like) due to such physical limitations. However, the utilization of such colorants is highly desired for a number of reasons, foremost the actual colorations available from such specific compounds.
The standard types of polymeric colorants now utilized within plastics (be they thermoplastics or thermoset types) are primarily poly(oxyalkylenated) compounds, such as triphenylmethanes, methines, and the like (i.e., those found within U.S. Pat. No. 4,992,204, to Kluger et al.). Some of these colorants exhibit certain problems in association with the catalysts utilized to effectuate plastic formation. For example, the triphenylmethane and methine moieties of such colorants are susceptible to attack by nucleophilic catalysts and their residues. As a result, the colorations provided by such polymeric colorants may be reduced in strength or changed in shade under such circumstances.
There is thus a desire to introduce such polymeric colorants having bis-acetoacetanilide groups therein within different types of compositions and therefore a desire to provide a bis-acetoacetanilide-type colorant containing polyoxyalkylene chains that can be tailored for versatility. Furthermore, there is a need to provide a colorant for introduction within thermoplastic and thermoset compositions which is far less susceptible to degradation due to attack by basic catalyst residues than the standard poly(oxyalkylenated) colorants of use today. To date, there have been no teachings or fair suggestions of such a highly desirable, specific polymeric bisacetoacetanilide colorant within the pertinent prior art or within the colorant industry itself.
DESCRIPTION OF THE INVENTION
It is thus an object of the invention to provide base stable yellow polymeric colorants for utilization within thermoplastic and thermoset articles. Another object of this invention to provide a yellow polymeric colorant exhibiting amide groups rather than base-susceptible methine moieties, which are thus less susceptible to attack by basic thermoplastic and thermoset catalysts, are easy to process, mixes well within target plastics, and provides excellent colorations within the target finished articles. Yet another object of this invention is to provide excellent colorations within liquid compositions (such as inks, and the like) through the utilization of water-soluble, liquid polymeric colorants, as noted above.
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 terms substituted phenyl and substituted polyphenyl are 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 poly(oxyalkylenated) acetoacetanilide azo colorants, particularly of the structure of Formula (I)
wherein R is alkyl, phenyl, polyphenyl, substituted phenyl, or substituted polyphenyl; E is hydrogen alkyl, halogen, alkoxy, or phenyl; a is 0, 1, or 2, wherein if a is 0 then A is phenyl, polyphenyl, substituted polyphenyl, or substituted phenyl, 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 of hydrogen; B is R″(gly)
w
[(EO)
x
(PO)
y
(EO)
2
EG]
n″
wherein EG is H or a moiety of Structure (III)
wherein R
4
is C
1
-C
12
alkyl or phenyl; all wherein gly is glycidol, EO is ethylene oxide, and PO is selected from the group consisting of propylene oxide, butylene oxide, and any mixtures or combinations thereof, n is 1 to 4, and wherein R″ is O, N, SO
2
N, methylene, S, N(R
5
), wherein R
5
is alkyl; wherein if R″ is O or SO
2
N then w=0 or 1, x=0-30, y=0-30, and z=0-30, wherein w+x+y+z>2, and if R″ is other than O or SO
2
N, then w=0-2, x=0-30, y=0-30, and z=0-30, wherein w+x+y+z>2; and wherein R′″ is halogen, hydrogen, alkyl, alkoxy, or B.
The present invention also preferably encompasses poly(oxyalkylenated) acetoacetanilide azo colorants of the structure of Formula (IV)
wherein R is phenyl, polyphenyl, substituted polyphenyl, or substituted phenyl; R′ is alkyl, phenyl, substituted phenyl, or polyphenyl; A is C
1
to C
20
alkyl, alkox ether, (EO)
k
(PO)
l
(EO)
m
, or (PO)
p
(EO)
q
(PO)
r
, wherein k=0-30, 1=0-30, m=0-30, wherein k+l+m>1, and wherein p=0-30, q=0-30, and r=0-30, wherein p+q+r>1; wherein B is R″(gly)
w
[(EO)
x
(PO)
y
(EO)
z
EG]
n″
wherein EG is H or a moiety of Structure (III)
wherein R
4
is C
1
-C
40
alkyl or phenyl; all wherein gly is glycidol, EO is ethylene oxide, and PO is selected from the group consisting of propylene oxide, butylene oxide, and any mixtures or combinations thereof, n is 1 to 4, and wherein R″ is O, N, SO
2
N, methylene, S, N(R
5
), wherein R
5
is alkyl or H; wherein if R″ is O, S, or SO
2
N then w=0 or 1, x=0-30, y=0-30, and z=0-30, wherein w+x+y+z>2, and if R″ is other than O, S, or SO
2
N, then w=0-2, x=0-30, y=0-30, and z=0-30, wherein w+x+y+z>2; and wherein R′″ is halogen, hydrogen, alkyl, alkoxy, or B.
Basically, such a colorant comprises a chromophore having two azo acetoacetanilide moieties and at least two poly(oxyalkylene) chains. Such a compound is prepared by diazotizing an aromatic amine compound, which comprises such poly(oxyalkylene) chains, in reaction with a compound conforming with the formula of Structure (V)
wherein R is alkyl, phenyl, polyphenyl, or substituted phenyl; E is H, halogen, alkyl, alkoxy, or phenyl; a is 0, 1, or 2, wherein if a is 0 then A is phenyl, polyphenyl, substituted polyphenyl, or substituted phenyl, 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 of hydrogen.
Preferably, the poly(oxyalkylene) chains of the inventive colorant comprise nucleophilic terminal groups capable of reacting with at least a portion of certain monomers which couple with bisac

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