US 5,290,921 A · Intermediates and colorants having primary hydroxyl enriched poly (oxyalkylene) moieties and their preparation

Abstract

The present invention provides primary hydroxyl enhanced colorants having markedly improved reactivities in e.g., polyurethane foams for imparting permanent coloring thereto, the colorants having the formula C--(Z).sub.1-4 are provided wherein C is an azo, methine, or azamethine chromogen and Z is a poly(oxyalkylene) moiety comprised of (1) at least two (A) units independently selected from those of the formulae --CH.sub.2 CH(O--T)CH.sub.2 O-- or --CH.sub.2 CH(O--T)CH.sub.2 O--T and (2) from none to about 200 (B) units of the formula (--RO--) wherein R is straight or branched chain hydrocarbon of 2-4 carbons, T is a moiety of the formula --CH.sub.2 CH(R.sub.1)--O--(RO).sub.0-40 --CH.sub.2 CH.sub.2 OH wherein R.sub.1 is selected from unsubstituted or substituted alkyl, aryl, alkenyloxyalkyl, alkoxyalkyl or aryloxyalkyl, and wherein the A units comprise at least 0.5 percent of the total A+B units.

Claims12

Dependent claims

A primary hydroxyl enhanced colorant of the formula:

C--(Z).sub.1-4
wherein C is an azo chromogen, and Z is a poly(oxyalkylene) moiety comprising the residue of at least two moles of glycidol reacted with an amino group of said chromogen, the residue of at least one mole of a secondary hydroxyl forming alkylene oxide selected from propylene oxide and butylene oxide reacted with each primary hydroxyl site of said glycidol residues, and at least one mole of ethylene oxide reacted with each secondary hydroxyl site present on said glycidol residues and said secondary hydroxyl forming alkylene oxide, provided that the total number of residues of said secondary hydroxyl forming alkylene oxides and said ethylene oxide does not exceed 200.

A primary hydroxyl enhanced colorant of the formula

C--(Z).sub.1-4
wherein C is an azo chromogen having the formula
Q--N.dbd.N--Ar
wherein Q is the residue of a carbocyclic or heterocyclic aromatic, diazotizable amine reactant, and Ar is the residue of carbocyclic or heterocyclic coupling component and wherein at least one --Z moiety is present on either Q-- or --Ar;
and Z is a poly(oxyalkylene) moiety comprised of (1) at least two (A) units independently selected from those of the formulae
--CH.sub.2 CH(O--T)CH.sub.2 O-- or --CH.sub.2 CH(O--T)CH.sub.2 O--T
and (2) from none to about 200 (B) units of the formula (--RO--) wherein R is straight or branched chain hydrocarbon of 2-4 carbons, T is a moiety of the formula
--CH.sub.2 CH(R.sub.1)--O--(RO).sub.0-40 --CH.sub.2 CH.sub.2 OH
and wherein R.sub.1 is selected from unsubstituted or substituted alkyl, aryl, alkenyloxyalkyl, alkoxyalkyl or aryloxyalkyl and said A units comprise at least 0.5 percent of the total A+B units.

6 more elements

A primary hydroxyl enhanced colorant of the formula

C--(Z).sub.1-4
wherein C is an azo chromogen having the formula
D--N.dbd.N--Ar
wherein D is an aromatic heterocyclic radical which contains a quaternary nitrogen atom, said radical being selected from unsubstituted or substituted:
thiazol-2-yl;
benzothiazol-2-yl;
1,3,4-thiadiazol-2-yl;
1,2,4-thiadizol-5-yl;
isothiazol-5-yl;
2,1-benzisothiazol-3-yl;
pyrazol-5-yl;
1,3,4-triazol-2-yl;
3- or 4-pyridyl;
or 4,5-(3,3-dimethyl-1-oxotetramethylene)-thiazol-2-yl;
wherein Ar is an aromatic amine residue selected from substituted or unsubstituted:
anilines;
naphthylamines;
1,2,3,4-tetrahydroquinolines;
3,4-dihydro-2H-1,4-benzoxazines;
2-aminothiazoles;
2,3-dihydroindoles;
carbazoles;
phenoxazines;
phenothiazines;
2-aminothiophenes or julolidines;
and wherein said compound contains at least one --Z moiety;
and Z is a poly(oxyalkylene) moiety comprised of (1) at least two (A) units independently selected from those of the formulae
--CH.sub.2 CH(O--T)CH.sub.2 O-- or --CH.sub.2 CH(O--T)CH.sub.2 O--T
and (2) from none to about 200 (B) units of the formula (--RO--) wherein R is straight or branched chain hydrocarbon of 2-4 carbons, T is a moiety of the formula
--CH.sub.2 CH(R.sub.1)--O--(RO).sub.0-40 --CH.sub.2 CH.sub.2 OH
and wherein R.sub.1 is selected from unsubstituted or substituted alkyl, aryl, alkenyloxyalkyl, alkoxyalkyl or aryloxyalkyl and said A units comprise at least 0.5 percent of the total A+B units.

28 more elements

Dependencies are inferred from the claim text.

Intermediates and colorants having primary hydroxyl enriched poly (oxyalkylene) moieties and their preparation

Life of this patent

Intermediates and colorants having primary hydroxyl enriched poly (oxyalkylene) moieties and their preparation

Life of this patent

Abstract

Claims12