Polymeric bis-acetoacetanilide azo colorants

Inactive Publication Date: 2002-10-31
MILLIKEN & CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

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.
Some of these colorants exhibit certain problems in association with the catalysts utilized to effectuate plasti

Method used

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  • Polymeric bis-acetoacetanilide azo colorants
  • Polymeric bis-acetoacetanilide azo colorants
  • Polymeric bis-acetoacetanilide azo colorants

Examples

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Effect test

example 1

[0028] 9

[0029] Ethanol (200 proof, 515 g) and p-aminophenol (300 g, 2.75 mol) were charged into a 2 L 3-neck round bottom flask equipped with a thermometer and a condenser. Benzaldehyde (292 g, 2.75 mol) was added from an additional funnel while maintaining a slow and steady flow and stirring. Another portion of ethanol (150 g) was added and the whole mixture was heated to reflux for 1.5 h. After cooling down to room temperature, the solid thus formed was collected by filtration and washed three times with ethanol (3.times.50 ml) and dried. 492 g (91%) of the imine product (structure above) was obtained as a pale yellow powder.

example 2

[0030] 10

[0031] The imine product (285 g, 1.44 mol) from Example 1, toluene (200 ml) and KOH (6 g) were charged into a one-gallon stainless steel reactor. After being purged 3 times to 60 psi with nitrogen, the reaction mixture was heated to 250.degree. F. and ethylene oxide (635 g, 14.4 mol) was added over a period of 2 hours. The mixture was then cooled down to room temperature and the toluene was stripped to yield 910 g (98.2%) of pale brown yellow liquid polyethylene glycol (10) imine (structure above).

example 3

[0032] 11

[0033] The imine (340 g, 0.27 mol) from Example 2 and water (150 g) were charged into a 1000-ml 3-neck flask. Concentrated hydrochloric acid (56 g) was added carefully while stirring and maintaining the temperature below 45.degree. C. After stirred for 30 min at 50.degree. C., the mixture was transferred into a 1000-ml flask and stripped by a rotary evaporator at 85-95.degree. C. for 1.5 hour. After cooling down to room temperature, 240 g of water was charged into the reaction mixture and the whole was stripped at 85-95.degree. C. for 1.5 hour. Then another 240 g of water was added and the mixture was stripped at 85-95.degree. C. till all of the water and benzaldehyde were removed. 285 g (97%) of product polyethylene glycol (10) aniline (structure above) was obtained as a light brownish yellow liquid.

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Abstract

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 extremely 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.

Description

[0001] This application is based upon provisional application No. 60 / 253,773 filed on Nov. 29, 2000.[0002] 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[0003] All U.S. patents cited within this specification are hereby incorporated by reference.[0004] Bis-acetoacetanilide azo pigments, dyes, and dyestuffs g...

Claims

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Application Information

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IPC IPC(8): C09B33/153C09B43/32C09B69/00C09B69/10
CPCC09B69/106C09B69/00
Inventor XIA, JUSONGSTEPHENS, ERIC B.MASON, MARY G.MILEY, JOHN W.STARKS, LEONARD J.
Owner MILLIKEN & CO
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