Dye intermediates

Details Dye intermediates Dye intermediates

1998-05-20

1999-10-26

Richter, Johann

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

Organic compounds

Sulfate esters

558 51, 558184, 560254, 560308, 564440, C07C30512

Patent

active

059731788

DESCRIPTION:

BRIEF SUMMARY
BACKGROUND OF THE INVENTION



TECHNICAL FIELD

This invention is directed to the field of fiber reactive dye intermediates useful in the preparation of fiber reactive dyes. Fiber reactive dyes containing the reactive vinyl sulfone moiety are well known; see e.g. U.S. Pat. No. 2,657,205. The vinyl sulfone moiety may be represented by the formula: --SO.sub.2 --CH.dbd.CH.sub.2. The vinyl group forms a covalent bond with pendant hydroxy or amine groups in the substrate which is to be dyed yielding dyeing of exceptional fastness.
Generally, the vinyl sulfone group is incorporated into the dye molecule by forming an amine containing at one least one vinyl sulfone group. The amine is then diazotized and coupled with a coupling component to form the dyestuff or it may be condensed with a dyestuff containing labile halogen moiety. Fiber reactive dyes containing the vinyl sulfone moiety such as monoazo, disazo, polyazo dyes, their metal complexes, the anthraquinone dyes, the phthalocyanine dyes, the formazan dyes and the dioxazine dyes are well known.


SUMMARY OF THE INVENTION

This invention is that of a new dye intermediate of the formula: ##STR2## wherein: A is selected from hydrogen, a substituted or unsubstituted alkyl of 1 to 4 carbon atoms, a substituted or unsubstituted alkoxy of 1 to 4 carbons, or a substituted or unsubstituted phenyl; from --OSO.sub.3 H, --OCOCH.sub.3,--OPO.sub.3 H,--Cl and


DESCRIPTION OF THE PREFERRED EMBODIMENTS

The dye intermediates of this invention have the formula: ##STR3## wherein: A is selected from hydrogen, a substituted and unsubstituted and unsubstituted C.sub.1 to C.sub.4 alkyl, a substituted and unsubstituted C.sub.1 to C.sub.4 alkoxy and a substituted or unsubstituted phenyl; --OSO.sub.3 H, --SSO.sub.3 H, --OPO.sub.3 H, --OCOCH.sub.2 --CH.sub.3, Cl, Br, F;
The moiety A may be substituted with one or more substituents such as --SO.sub.3 H, --COOH, cyano, hydroxy, sulfamoyl, halogen (Cl, F, Br), ethoxy, methoxy and the like, preferably A is methyl or hydrogen, most preferably hydrogen. Similarly, the moiety W may be substituted with one or more substituents such as sulfo, carboxy, hydroxy, halogen, cyano, cyanamid, methyl, ethyl, propyl, methoxy, ethoxy, propoxy; preferably W is phenylene substituted with at least one sulfo group. The dye intermediates of this invention are shown herein in their free acid form but it is apparent to one of ordinary skill in the art that they can and are useable in their free acid and soluble salt forms.
The dye intermediates of this invention can be used to prepare fiber reactive dyes by known methods. The term fiber reactive dyes is intended to mean dyes that are capable of forming a covalent bond with the substrate that is being dyed; e.g. by reacting with the hydroxyl group of a cellulosic fiber or with the reactive groups in natural and synthetic polyamides. These fiber reactive dyes may be represented by the general formula: ##STR4## wherein: D represents a radical of dye such as a monoazo, disazo, polyazo dye or a metal complex thereof or anthraquinone, phthalocyanine, formazan or dioxazine dye; are as defined above.
The new dye intermediates of the invention may be prepared from vinyl sulfone substituted phenylamine or naphthylamine. The amine moiety is first acylated using an acyl anhydride or acid chloride; preferably the amine moiety is acetylated using acetic anhydride. The acylated, vinyl sulfone substituted amine is then reacted with an equimolar amount of mercaptoethanol. The resulting sulfide compound is then oxidized using an oxidizing agent such as hydrogen peroxide in the presence of a catalyst such as sodium tungstate to yield the sulfone having the general formula: AR--SO.sub.2 --(CH.sub.2).sub.2 --SO.sub.2 --(CH.sub.2).sub.2 OH; wherein "AR" is a phenyl or naphthyl amide. The amide is deacylated and esterified, preferably the esterification is done in sulfuric acid to yield the sulfato ester.
The following examples illustrate the preparation of dye intermediates according to the invention:


EXAMPLE 1
107 parts of ace

REFERENCES:
patent: 3301884 (1967-01-01), Meininger et al.
patent: 5155271 (1992-10-01), Aeschlimann et al.
The Merck Index, 11.sup.th Edition, "An Encyclopedia of Chemicals, Drugs, and Biologicals", Edited by S. Budavari, Rahway, NJ: Merck & Co., Inc., 1989, No. 510 (p. 81). No. 3100 (p. 491).

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