Bismethine benzodifuranone derivative colorants

Details Bismethine benzodifuranone derivative colorants Bismethine benzodifuranone derivative colorants

2001-09-18

2002-12-10

Owens, Amelia (Department: 1625)

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C549S297000

Reexamination Certificate

active

06492533

ABSTRACT:

FIELD OF THE INVENTION
This invention relates to colorants comprising a chromophore having two methine moieties attached to a benzodifuranone backbone, wherein said moieties optionally have at least one poly(oxyalkylene) chain, preferably at least two such chains attached thereto. Such colorants exhibit excellent thermal stability, effective colorations, excellent low extraction rates, and effective lightfastness levels, particularly when incorporated within certain media and/or on the surface of certain substrates, particularly polyesters. The optional poly(oxyalkylene) chains also increase the solubility in different solvents or resins thereby permitting the introduction of such excellent coloring chromophores within diverse media and/or on diverse substrates as well as provides a liquid colorant which facilitates handling. 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.
There continues to be a need to provide versatile colorants within various applications such that the coloring agent itself exhibits excellent colorations (particularly at low color loadings and due to inherently high quantum absorption efficiency), high thermal stability, effective lightfastness, low extraction (or drastic reduction in possibility of removal therefrom via extraction by solvents or like sources), ease in handling, ability to mix thoroughly with other coloring agents and thus to provide effective different hues and tints within or on target substrates, and acceptable toxicity levels. There has been a need to provide improved colorants meeting this criteria for certain thermoplastic media, such as polyesters, such that the colorants themselves exhibit excellent compatibility therein (for instance in terms of intrinsic viscosity loss and the other characteristics desired for such plastics as noted above). In particular, such characteristics for polyesters are desired for colorants that absorb, for example, though not necessarily, within the red portion of the visible spectrum. Other hues are available as well for such a desired, high-performing polyester plastic colorant, including blue, yellow, orange, and the like, all dependent on the presence of certain coupling or modifying moieties present on the chromophore backbone itself. It is believed and, as noted above, has been determined that such desirable polyester plastic colorations with the characteristics noted above are possible through the addition of certain pendant groups to the chromophore backbone which do not act as couplers or color modifiers [such as, for example poly(oxyalkylene) groups] and thus any chromophore (and resultant hue or tint) may be utilized with the desired benzodifuranone bismethine chromophore itself.
Previous coloring agents for such end-uses have included pigments, dyes, or dyestuffs, with each having its own drawback, be it an extraction problem from the finished article, a handling problem during manufacturing due to solid dust particles, a staining problem, due to the difficulty associated with cleaning such coloring agents from manufacturing machinery after colored plastic production, and other like issues. As a result, there is a clear desire to provide easier to handle, less extractable, easy-to-clean, etc., coloring agents for introduction within thermoplastic articles to provide decorative, aesthetic, and other like effects. However, the chromophores present within such dyes, pigments, and the like, are highly desired for the hues and shades they provide within the ultimate thermoplastic articles themselves. Facilitating the introduction of such chromophores within such formulations is thus a highly desired target within the colored thermoplastic industry, whether it be in terms of handling, extraction, cleaning, or the like.
Attempts to meet this desire have included the introduction of certain standard types of polymeric colorants within plastics (be they thermoplastics or thermoset types). These colorants 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 during incorporation into thermosets and thermoplastics. In thermoplastic compositions such as polyesters, many of these previously disclosed compositions are not stable at the polyester processing temperatures. As a result, the colorations provided by such polymeric colorants may be reduced in strength or changed in shade under such circumstances. Other types of colorants have been discussed within the prior art, such as azos and bisazos, but the specific colorations provided by such compounds are limited to certain hues and their utilization within polyesters is suspect from a number of perspectives (such as thermal stability, and the like). There is thus a desire to introduce new types of colorants comprising different types of chromophores for the purpose of providing new, effective, versatile colorants for such myriad end-uses as noted above and that exhibit excellent colorations, extraction, thermal stability, mixing with other coloring agents, and low toxicity, at least.
A certain class of colorants, namely benzodifuranone derivatives, exhibit excellent colorations and have been utilized within different applications, most prominently within inks, such as in U.S. Pat. No. 5,665,150 to Schwarz, and U.S. Pat. No. 5,779,778 to Gregory et al. and as disperse dyes for polyester, such as in
J. Soc. Dyers Colour
. 110, 1994, p, 178. The chromophores disclosed in this art are significantly structurally and thus electronically different from the inventive chromophores disclosed herein, exhibiting a substituted phenyl group attached directly to the benzodifuranone core structure, and thus cannot be classified as methines. There has also been some discussion of introducing isatin-based benzodifuranones within plastics as disclosed within published PCT Application WO00/24736 to Ciba Specialty Chemicals. Such compounds are limited to non-polymeric species and, again, require the presence of isatin as a substituent (and thus a heterocyclic pendant group attached to the double bond between such an isatin adduct and the backbone benzodifuranone compound). Apparently, such compounds provide effective colorations within plastics; however, there is no discussion of the handling issues, mixing capabilities with other colorants, migratory properties, lightfastness, or other concerns with colorants for plastics. Furthermore, the reaction with isatin is rather costly and the yield is suspect thus increasing the potential costs to the end-user and/or the consumer. A new type of benzodifuranone colorant for plastic applications (at least) is thus desirable, primarily due to the potential colorations provided by such base chromophores. Furthermore, simplified methods of producing such benzodifuranone derivatives are also desired such that the end colorant can be tailored in its constitution to any end-use application through the presence of poly(oxyalkylene) groups thereon. Such an option would thus provide much-needed versatility for such desirable coloring agents within various media (including the aforementioned plastics, liquids, foams, and the like). To date, there have been no teachings or fair suggestions of such a highly desirable, specific potentially polymeric benzodifuranone derivative 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 novel thermally stable polymeric colorants for utilization within thermoplastic and thermoset articles based on bismethine benzodifuranone backbone structures. Yet another object of this invention is to provide excellent colorations within liquid compositions (such as inks, and the like) through the utilization of the same bismethine benzodifuranone-type compounds a

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