Polymeric articles comprising novel bismethine benzodifuranone derivative colorants

a technology of bismethine benzodifuranone and derivatives, which is applied in the field of polymer articles comprising novel bismethine benzodifuranone derivative colorants, can solve the problems of colorants that exhibit certain problems, staining problems, and many of the previously disclosed compositions are not stable at the polyester processing temperatur

Inactive Publication Date: 2003-05-01
MILLIKEN & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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.
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).
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.
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.

Method used

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  • Polymeric articles comprising novel bismethine benzodifuranone derivative colorants
  • Polymeric articles comprising novel bismethine benzodifuranone derivative colorants
  • Polymeric articles comprising novel bismethine benzodifuranone derivative colorants

Examples

Experimental program
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Effect test

example 1

[0038] To a 250 mL round bottom flask containing 33.0 g of alkoxylated (2EO 10PO 6EO) para-formyl aniline was added glycine (0.36 g), 2,5-dihydroxy-1,4-benzenediacetic acid-di-gamma-lactone [produced in accordance with the method taught within Wood et al., Journal of the American Chemical Society, 66, 1541 (1944)] (2.98 g), and water (25 g). The ensuing reaction mixture was placed on a rotary evaporator and mixed for approximately 5 minutes. The reaction mixture was then heated to 90-95.degree. C. for 2.5 hours while a water aspirator vacuum was applied to the rotary evaporator. The ensuing red liquid was allowed to cool to ambient temperature overnight. Water (80 g) was then added to the product. The mixture was then stirred on the rotary evaporator and heated to 75-80.degree. C. The mixture was then poured into a separatory funnel and allowed to phase for 30 minutes during which time two layers formed. The bottom product layer was removed and mixed with an additional 80 g of water...

example 2

[0039] To a 250 mL round bottom flask containing 26.2 g of alkoxylated (10EO) aldehyde of 2,5-dimethoxyaniline was added glycine (0.35 g), 2,5-dihydroxy-1,4-benzenediacetic acid-di-gamma-lactone (4.03 g), and water (20 g). The ensuing reaction mixture was placed on a rotary evaporator and mixed for approximately 5 minutes. The reaction mixture was then heated to 90-95.degree. C. for 2.5 hours while a water aspirator vacuum was applied to the rotary evaporator. The ensuing blue liquid was allowed to cool to ambient temperature overnight. Water (20 g) was then added to the product. The reaction mixture was then heated to 90-95.degree. C. for 2 hours while a water aspirator vacuum was applied to the rotary evaporator to give a thick blue oil exhibiting a .lambda..sub.max absorbance (in methanol) of 581 nm.

example 3

[0040] To a 3-neck, 100 mL round bottom flask containing 30 g of alkoxylated (2EO 6PO 6EO) aldehyde of 2,5-dimethoxyaniline was added glycine (0.21 g), 2,5-dihydroxy-1,4-benzenediacetic acid-di-gamma-lactone (3.23 g), and water (10 g). The ensuing reaction mixture was heated to 80-85.degree. C. for 4 hours. The ensuing blue liquid was allowed to cool to ambient temperature and stir overnight. The mixture was then transferred to a 1-neck 250 mL round bottom flask and stripped on a rotoary evaporator for 2 hours at 90-95.degree. C. Water (90 g) was then added to the product. The solution was mixed and heated to 80.degree. C. before being poured into a separatory funnel. The solution was allowed to phase separate. The bottom product layer was drained and was again washed as above with 90 g of water. The ensuing product layer was stripped via rotary evaporator to give 26 g of a blue oil exhibiting a .lambda..sub.max absorbance (in methanol) of 577 nm.

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Abstract

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 are provided. 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.

Description

[0001] 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[0002] All U.S. patents cited...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C07D493/04C08K5/15C08K5/35C08K5/46C08K5/48C09B57/00C09B69/00
CPCC07D493/04C09B69/00C09B57/00
Inventor CONNOR, DANIEL M.STEPHENS, ERIC B.
Owner MILLIKEN & CO
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