Thermoplastic polymer composition containing dye compositions

Details Thermoplastic polymer composition containing dye compositions Thermoplastic polymer composition containing dye compositions

1999-05-11

2001-06-19

Sanders, Kriellion (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C544S337000, C106S287250, C106S498000

Reexamination Certificate

active

06248816

ABSTRACT:

INTRODUCTION
The present invention is directed to polymeric compositions for use as colorants in applications such as molded articles, films and fibers.
BACKGROUND OF INVENTION
In many applications where molding or spinning of precolored thermoplastic materials is used to prepare a colored article, it is desirable to have an evenly dispersed soluble dye in the resin as opposed to a pigment. Dyes commonly provide higher color strength, higher transparency and lower abrasion (in spinning of fibers) than pigments.
Attempts have been made to produce adequate dark colors, such as grays and black colors using organic dyes, usually by combining dyes of different colors, such as orange dyes and blue dyes. Unfortunately, these combinations require tedious process steps and produce products having inadequate color quantity. For instance, when a blue dye is mixed with an orange dye to form a black dye, the orange dye and the blue dye must fade at the same rate or the black will lose its color and exhibit an orange or blue tint. These and other problems have practically prevented the use of dyes as gray and black colorants in thermoplastic materials.
Because no true black dye exists and attempts at combining dyes of differing colors have been unsuccessful, black pigments, such as carbon black, have traditionally been used to generate black coloration in thermoplastic materials. While carbon black produces materials having high black color strength, the use of carbon black in the processing of black thermoplastic materials results in problems with clogging of filter packs and erosion of spinnerets.
In addition, when pigments or particles, such as carbon black, are used to color fine denier thermoplastic fibers, such as fibers of less than about 4.0 denier/filament, weak fibers that are susceptible to breaking and fragmenting are formed. These weak fine denier fibers are a result of the size of the particles in relation to the fibers. For instance, as the fiber size decreases, the particles consume more and more of the diameter of the fiber, decreasing the amount of fiber-fiber bond at the location of the particles. Hence, fine denier fibers containing pigment colorants generally result in fibers, which lack the strength for practical usage. Despite these drawbacks, pigments, especially carbon black, have been the black colorant of choice in thermoplastic materials.
It is apparent from the above that there is a need for colorants that provide and maintain high quality in thermoplastic materials, such as molded articles, films and fibers. Furthermore, there is a need for a dye composition that is small enough to function as a colorant for fine denier fibers, such as fibers of less that 4 denier/filament.
SUMMARY OF THE INVENTION
The present invention relates to a polymeric composition suitable for use in films, fibers and molded articles, where a soluble, easily dispersed colorant is desirable. The polymeric composition provides high color quality and is small enough to function as a colorant in microdenier fibers.
The polymeric composition comprises a mixture, such as a blend, of a thermoplastic resin and a dye composition. The thermoplastic resin is preferably present in the polymeric composition in an amount from about 50 weight percent to about 99.9 weight percent, and the dye composition is preferably present in an amount from about 0.1 weight percent to about 50 weight percent.
The dye composition contains an indanthrone compound as a major component. As used herein, indanthrone compounds are defined as a compounds having the general structure represented by Formula I:
wherein R is hydrogen or at least one group independently selected from C
1
-C
8
alkyl, C
1
-C
8
alkoxy, halogen, hydroxy, trifluoromethyl, aryloxy, arylthio, arylamino, C
1
-C
8
carbalkoxy, —CO
2
H, C
1
-C
8
alkanoyloxy, arylazo, —CN, —NO
2
, —SO
2
-C
1
-C
8
alkyl, —SO
2
N(R1)R2, and —CON(R1)R2, wherein R1 and R2 are independently selected from C
1
-C
8
alkyl, C
3
-C
8
cycloalkyl, aryl and hydrogen.
Depending on the amount of the dye composition represented by Formula I that is present in the polymeric composition, the polymeric composition may exhibit a color of differing shades of green and black. The greater the amount of dye composition present in the polymeric composition, the darker the polymeric composition will appear. It is noted that these colors are subjective qualities and will depend on the person viewing the polymeric composition.
The polymeric composition is preferably prepared by combining a dye composition with a thermoplastic resin to form a mixture using any suitable process known in the art, and then melt blending the mixture to form the polymeric composition. Melt blending the composition can be accomplished by any suitable process known in the art including admixing the dye composition with the thermoplastic resin. The melt blending process is preferably performed in an extruder.
Alternatively, the polymeric composition comprises the reaction products of at least one diacid component or its ester forming derivative, at least one diol component, and the dye composition represented by Formula I, wherein R is a reactive group capable of being copolymerized polymeric compositions. As used herein, the term “reactive group” includes hydroxy, carboxy, C
1
to C
8
carbalkoxy and C
1
to C
8
alkanoyloxy. The reaction used to prepare the polymeric composition is preferably a copolymerization process.
The copolymerization process preferably comprises combining at least one diacid component or its ester derivative, at least one diol component and the dye composition to form a mixture; and polymerizing the mixture to form a polymeric composition containing the dye composition in an amount from about 0.1 to about 30 weight percent.
As used herein, the term “polymeric composition” is used to define polymeric compositions comprising a dye composition, whether it be in the form of a mixture, blend or the product of a reaction. The present invention is further directed to thermoplastic articles containing polymeric compositions and processes for preparing thermoplastic articles containing polymeric compositions. Thermoplastic articles within the scope of the present invention include moldable articles, films and fibers. Molded articles as defined herein are articles formed by standard molding processes, including: injection molding, thermoforming, extrusion blow molding, injection blow molding, and reheat blow molding.
The present invention is especially useful for the manufacture of fine denier fibers and methods for preparing fine denier fibers containing polymeric compositions. As defined in the present invention, fine denier fibers are fibers having a denier no greater than about 4. For example, melt spun fiber can be prepared using the polymeric compositions. Because the polymeric compositions are used as opposed to pigments or particles, the melt spun fiber formed can be spun in a variety of weights including fine denier fiber (<4.0 denier/filament) and even very fine “microdenier” fiber (<1.0 denier/filament) with no loss in fiber quality.
Additionally, the present invention is directed to a process for preparing a dye composition. In particular, the present invention is directed to a novel process for preparing the dye composition in a single reaction vessel. The dye composition is prepared by reacting 1-amino-2,4dibromo-9,10-anthraquinone and an aromatic amine having the general formula:
wherein R is defined above, to form 1-amino-2-bromo-4-arylamino-9,10-anthra-quinones. The 1-amino-2-bromo-4-aryl-amino-9,10-anthraquinones are then coupled in an alkyl benzoate solvent in the presence of a copper catalyst to form a dye composition.
Still further, the present invention is directed to a novel black-like dye composition. It has been discovered that when R is an aryloxy functional group, the black dye composition exhibits unexpected qualities, such as solubility in the thermoplastic resin and an increased black color.
These and other advantages and features of the present invention will become

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