Colored polymers

Details Colored polymers Colored polymers

1998-02-12

2000-03-21

Cameron, Erma

Coating processes

Solid particles or fibers applied

Localized different areas produced

8507, 8647, 427280, 4273855, 106 20C, 106 20D, B05D 100

Patent

active

060400056

DESCRIPTION:

BRIEF SUMMARY
This invention relates to coloured filters and to coloured polymers, their preparation and uses in various applications, including the colouration of plastics, inks and coloured reprographic toners.
U.S. Pat. No. 5,231,135 describes a method for forming a coloured polymer coating on a substrate, for example an automobile, in which a reactive acrylic polymer containing some reactive colourant and a linking agent is applied to the substrate and allowed to cross-link. The coatings so formed are used to protect the underlying substrates from wear and exposure to sunlight and the elements.
We have now found that valuable colorants can be prepared by polymerisation of certain dyes and triazine compounds. These colorants are useful for plastics, toners and in particular inks.
According to the present invention there is provided a coloured polymer obtained or obtainable by polymerisation of a mixture consisting essentially of a dye and a triazine compound having at least two groups selected from alkoxymethylamino and hydroxymethylamino. Preferably the triazine compound has 2 or 3 groups selected from alkoxymethylamino and hydroxymethylamino. The alkoxymethylamino and hydroxymethylamino groups which are present on the triazine compound are preferably of the formula --N(R.sup.a)(CH.sub.2 OR.sup.b) wherein each R.sup.a and R.sup.b independently is H, alkyl (preferably C.sub.1-6 -alkyl), alkoxyalkyl (preferably --(CH.sub.2).sub.m --O(CH.sub.2).sub.n CH.sub.3 wherein m is from 1 to 6 and n is from 0 to 5), aryl (preferably phenyl) or hydroxyalkyl (preferably --(CH.sub.2).sub.m OH wherein m is as hereinbefore defined).
A preferred triazine compound having at least two groups selected from alkoxymethylamino and hydroxymethylamino is of the Formula (A): ##STR1## wherein R.sup.c is alkyl, aryl or preferably a group of formula --N(R.sup.a)(CH.sub.2 OR.sup.b), and each R.sup.a and R.sup.b independently is as hereinbefore defined.
In a preferred embodiment R.sup.c is C.sub.1-6 -alkyl, C.sub.6-12 -aryl or preferably --N(R.sup.a)(CH.sub.2 OR.sup.b) as hereinbefore defined. Preferably each R.sup.a is H and each R.sup.b is methyl. A particularly preferred triazine compound is tri(methoxymethylamino)-1,3,5-triazine.
The mixture of said dye and triazine compound may contain small quantities of other ingredients which are reactive towards the dye and/or the triazine compound, but it is preferred that the amount of these ingredients is less than 20%, preferably less than 10%, more preferably less than 5% by weight relative to the total weight of dye and triazine compound. It is particularly preferred that the dye and said triazine compound are the only components in the mixture which polymerise to form the coloured polymer. In this way, the polymerisation process is simplified and the resultant polymer is easy to isolate, formulate, handle and has a strong colour. The mixture may contain components which do not form part of the coloured polymer, for example a catalyst or diluents or solvents in which polymerisation takes place.
During polymerisation the dye and the triazine compound react with each other to give the desired coloured polymer. Thus a dye is chosen which has a group which is reactive towards said triazine compound, for example a --SH, primary amino, secondary amino, hydroxy, epoxide, acid, acid halide, labile ester or an activated vinyl group. Preferably the primary amino, secondary amino and hydroxy groups are not attached to aromatic carbon atoms because this lowers their reactivity towards said triazine compound. Activated vinyl groups are preferably of the formula --COCH.dbd.CH.sub.2 or --SO.sub.2 CH.dbd.CH.sub.2.
Preferred classes of dyes which may be used are dyes of the azo (preferably monoazo or disazo), azomethine, triphenodioxazine, phthalocyanine, benzodifuranone, anthraquinone, indigoid, polymethine quinophthalone, pyrroline and benzofuranone series, provided of course that the dye has a group which is reactive towards said triazine compound.
A preferred dye is an azo dye which is reactive towards said triaz

REFERENCES:
patent: 3458271 (1969-07-01), Ito et al.
patent: 4351871 (1982-09-01), Lewis et al.
patent: 5231135 (1993-07-01), Machell et al.
Yarmosh et al, Izv. Vyssh. Ucheb. Zaved. Tekhnol. Legk. Prom. 1971, (3), pp 66-68.
Yarmosh et al, Kozh.-Obuv. Prom. (1972), 14(2), pp 29-31.
Chemical Abstracts, vol. 75, No. 20, Nov. 15, 1971, abstract No. 119220k; Yarmosh et al: "Reaction of methylol derivatives of melamines with dyes", p. 47; XP002018789 see abstract & Izv. Vyssh. Ucheb. Zaved., Tekhnol. Legk. Rpom., No. 3, 1971, pp. 66-68.

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