This invention relates to heterocyclic red azo colorants for seed treatment applications. The red azo colorants contain a heterocycle that includes one nitrogen atom and one sulfur atom and are free from electron-withdrawing groups on the heterocycle. Seeds for use in horticultural/agriculture applications that are coated with the heterocyclic azo colorants provide anti-counterfeiting properties to the coated seeds. A color change phenomenon is observed when the coated seeds are exposed to an acidic material, such as vinegar, and provides evidence of the authenticity of the coated seeds. The invention also relates to agricultural formulations containing the heterocyclic red azo colorants that can be used as an anti-counterfeit agents.

This invention relates to heterocyclic red azo colorants for seed treatment applications. The red azo colorants contain a heterocycle that includes one nitrogen atom and one sulfur atom and are free from electron-withdrawing groups on the heterocycle. Seeds for use in horticultural/agriculture applications that are coated with the heterocyclic azo colorants provide anti-counterfeiting properties to the coated seeds. A color change phenomenon is observed when the coated seeds are exposed to an acidic material, such as vinegar, and provides evidence of the authenticity of the coated seeds. The invention also relates to agricultural formulations containing the heterocyclic red azo colorants that can be used as an anti-counterfeit agents.

A compound represented by formula: is disclosed. R is hydrogen or alkyl; X is alkylene; Y is a bond, ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, thiourea, alkylene, arylalkylene, alkylarylene, or arylene, wherein alkylene, arylalkylene, alkylarylene, and arylene are optionally at least one of interrupted or terminated by at least one of an ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, or thiourea; and Z is an acrylate, a methacrylate, an acrylamide, a methacrylamide, a styrenyl, or a terminal alkenylene having at least three carbon atoms. A composition including the compound, and a method of determining the degree of cure of a curable polymeric resin are also disclosed. ##STR00001##

The disclosure relates to a method for improving the alkali resistance and oxidation resistance of a benzothiazole disperse dye, and belongs to the field of disperse dyes. In the disclosure, 4 kinds of diazo components and 8 kinds of coupling components are used in designing and synthesizing 28 thiazole heterocyclic azo disperse dyes, and the alkali resistance and oxidation resistance of the disperse dyes are improved. Structure confirmation is performed on the synthetic disperse dyes, and the alkali resistance, oxidation resistance and other dyeing properties of the disperse dyes are tested. According to the method for improving the alkali resistance and oxidation resistance of the benzothiazole disperse dye provided in the disclosure, a relationship between a dye structure and the alkali resistance and oxidation resistance is determined, the disperse dyes with excellent alkali resistance and oxidation resistance are obtained, and the dyeing performance is stable under a dyeing condition of 10 g/L of sodium hydroxide or 5 g/L of hydrogen peroxide. This kind of dyes can be applied to a one bath for bleaching and dyeing of polyester and cotton and a one bath for deweighting and dyeing of polyester, dyeing and finishing in a short process are achieved, and great ecological and economic benefits are obtained.

Disclosed is an azo compound represented by Formula (I)

##STR00001##

in which R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or methyl, and R.sup.3 is hydrogen, an unsubstituted linear alkyl group of from 1 to 4 carbon atoms, or an unsubstituted branched alkyl group of from 1 to 9 carbon atoms. This disclosure also provides a black dye composition including the azo compound represented by Formula (I).

Disclosed is an azo compound represented by Formula (I), ##STR00001##
in which R.sup.1 is hydrogen or methyl, R.sup.2 is hydrogen or methyl, and R.sup.3 is hydrogen, an unsubstituted linear alkyl group of from 1 to 4 carbon atoms, or an unsubstituted branched alkyl group of from 1 to 4 carbon atoms. This disclosure also provides a black dye composition including the azo compound represented by Formula (I).

A compound represented by formula:

##STR00001##

and a treated filler having the compound on at least a portion of its surface. R is hydrogen or alkyl. X is alkylene, arylalkylene, or alkylarylene, each optionally interrupted by at least one of an ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, or thiourea, with alkylene optionally interrupted by arylene. W is hydroxyl, a sulfonic acid group, a phosphonic acid group, carboxylic acid group, NHR.sup.1, epoxy, or Si(Y).sub.x(Z).sub.3-x. Y is alkyl, aryl, arylalkylenyl, or alkylarylenyl. Z is halide, hydroxyl, alkoxy, aryloxy, acyloxy, polyalkyleneoxy, O covalently bonded to the surface of the filler, or O bonded to another silicon atom, and x is 0 or 1. A composition including the treated filler, a method of making the treated filler, and a method of determining the degree of cure of a curable polymeric resin are also disclosed.

A compound represented by formula (I): and a treated filler having the compound on at least a portion of its surface. R is hydrogen or alkyl. X is alkylene, arylalkylene, or alkylarylene, each optionally interrupted by at least one of an ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, or thiourea, with alkylene optionally interrupted by arylene. W is hydroxyl, a sulfonic acid group, a phosphonic acid group, carboxylic acid group, NHR.sup.1, epoxy, or Si(Y).sub.x(Z).sub.3-x. Y is alkyl, aryl, arylalkylenyl, or alkylarylenyl. Z is halide, hydroxyl, alkoxy aryloxy, acyloxy, polyalkyleneoxy, O covalently bonded to the surface of the filler, or O bonded to another silicon atom, and x is 0 or 1. A composition including the treated filler, a method of making the treated filler, and a method of determining the degree of cure of a curable polymeric resin are also disclosed. ##STR00001##

A curable composition having a polythiol; at least one unsaturated compound comprising more than one carbon-carbon double bond, carbon-carbon triple bond, or a combination thereof; and a dye compound represented by formula (I). A crosslinked composition prepared from the curable composition, a method of making an at least partially crosslinked network, a method for indicating curing in a curable composition, and a method of stabilizing a curable composition comprising a polythiol and at least one unsaturated compound comprising more than one carbon-carbon double bond, carbon-carbon triple bond, or a combination thereof are also disclosed. Z is not reactive with the polythiol or unsaturated compound.

##STR00001##

The disclosure relates to a method for improving the alkali resistance and oxidation resistance of a benzothiazole disperse dye, and belongs to the field of disperse dyes. In the disclosure, 4 kinds of diazo components and 8 kinds of coupling components are used in designing and synthesizing 28 thiazole heterocyclic azo disperse dyes, and the alkali resistance and oxidation resistance of the disperse dyes are improved. Structure confirmation is performed on the synthetic disperse dyes, and the alkali resistance, oxidation resistance and other dyeing properties of the disperse dyes are tested. According to the method for improving the alkali resistance and oxidation resistance of the benzothiazole disperse dye provided in the disclosure, a relationship between a dye structure and the alkali resistance and oxidation resistance is determined, the disperse dyes with excellent alkali resistance and oxidation resistance are obtained, and the dyeing performance is stable under a dyeing condition of 10 g/L of sodium hydroxide or 5 g/L of hydrogen peroxide. This kind of dyes can be applied to a one bath for bleaching and dyeing of polyester and cotton and a one bath for deweighting and dyeing of polyester, dyeing and finishing in a short process are achieved, and great ecological and economic benefits are obtained.