Colorants and intermediates therefor having branched poly(oxyalkylene)moieties, and their manufacture

Claim 2

A composition of claim 1 wherein the total number of said other epoxide residues is from about 150 to about 400 and the ratio of the total of -O-PO- AND -O-BO-linkages of all glycidol residues to the total of all functional oxy linkages of said glycidol residues is less than one.

Claim 3

A composition of claim 1 wherein the EO residues comprise from about 90 to 100 mole percent of said other epoxide residues.

Claim 4

A composition of claim 1 wherein the poly(oxyalkylene) moiety contains one glycidol residue segment containing 2-6 glycidol residues.

Claim 5

A composition of claim 1 wherein each said poly(oxyalkylene) moiety contains at least one glycidol residue segment having three separate poly(oxyalkylene) branches pendant therefrom.

Claim 6

A composition of claim 1 wherein each said poly(oxyalkylene) moiety is independently terminated by hydrogen or a group selected from acyl or unsubstituted or substituted alkyl, cycloalkyl, or aryl.

Claim 7

A composition of claim 5 wherein each said poly(oxyalkylene) branch is terminated by hydrogen.

Claim 8

A composition of claim 1 wherein the number of Z moieties is from 1-4.

Claim 9

A colorant composition of claim 1 wherein C is selected from compounds containing at least one chromogen radical selected from mono-, bis-, tris-, or tetrakis-azo, methine, azamethine, indophenol, or triphenylmethane chromogen radicals.

Claim 10

A monoazo compound of claim 1 having the formula wherein Q is the residue of a carbocyclic or heterocyclic aromatic, diazotizable amine reactant, Ar is the residue of a carbocyclic or heterocyclic coupling component, and wherein at least one -Z moiety is present in either Q- or -Ar.

Claim 11

An azo compound according to claim 10 wherein Q is selected from unsubstituted or substituted: phenyl; naphthyl; thiazol-2-yl; benzothiazol-2-yl; 1,3,4-thiadiazol-2-yl; 1,2,4,-thiadiazol-5-yl; isothiazol-5-yl; isoxazol-5-yl; 2,1-benzisothiazol-3-yl; 2-thienyl; 3-and 4-pyridyl; pyrazol-5-yl; 3-and 4-phthalimidyl; 1,2,4-triazol-3-yl; or 4,5 (3,3-dimethyl-1-oxotetramethylene)thiazol-2-yl.

Claim 12

A compound of claim 1 having the formula wherein Ar is the residue of a carbocyclic or heterocyclic coupling component; and Q₁ is a di- or trivalent aromatic, carbocyclic or heterocyclic moiety and wherein at least one -Z moiety is present in either Q₁ or -Ar.

Claim 13

A compound of claim 12 wherein Q₁ is selected from unsubstituted or substituted mono- or multi-carbocyclic aromatic moieties, aromatic heterocyclic moieties, or two or more of said moieties interconnected by a di- or tri-valent linking group.

Claim 14

A compound of claim 13 wherein said linking group is selected from a covalent bond, substituted or unsubstituted lower alkylene, substituted or unsubstituted arylene, substituted or unsubstituted cycloalkylene, or any of the above in combination with one or more of any or a mixture or combination of nitrogen, sulfur, oxygen, carbonyl or thiocarbonyl.

Claim 15

A methine compound of claim 1 having the formula wherein: M is an active methylene residue; Ar is the residue of an electron rich aromatic carbocyclic or heterocyclic moiety, and wherein at least one -Z moiety is present in either -M or -Ar.

Claim 16

An azamethine compound of claim 1 having the formula wherein M is an active methylene residue; Ar is the residue of an electron rich aromatic carbocyclic or heterocyclic moiety, and wherein at least one -Z moiety is present in either -M or -Ar.

Claim 17

An indophenol compound of claim 1 having the formula wherein R₄₅ is hydrogen or 1-3 substituents selected from lower alkyl, lower alkoxy, halogen, or hydroxy; Ar is the residue of an electron rich aromatic carbocyclic or heterocyclic moiety, and wherein at least one -Z moiety is present in the compound.

Claim 18

A triaryl methane colorant of claim 1 having the formula wherein Ar is the residue of an electron rich aromatic carbocyclic or heterocyclic moiety; X⁻ is an anion selected from Cl⁻, Br⁻, or ZnCl₄⁻²/2, and wherein at least one -Z moiety is present in the compound.

Claim 19

A compound according to claim 11 wherein Q is selected from the radicals wherein: R₂ is hydrogen or 1-3 substituents selected from lower alkyl, lower alkoxy, halogen, cyano, nitro, formyl, alkanoyl, aroyl, thiocyano, lower alkylthio, arylthio, lower alkylsulfonyl, arylsulfonyl, -SO₃aryl, carbalkoxy, unsubstituted or substituted sulfamoyl, unsubstituted or substituted carbamoyl, nitro, trifluoromethyl or arylazo; R₃ is hydrogen or 1-2 substituents selected from lower alkyl, aryl, arylazo, halogen, cyano, formyl, carbalkoxy, nitro, thiocyano, lower alkylsulfonyl, arylsulfonyl, trifluoromethyl, alkanoyl, aroyl, unsubstituted or substituted sulfamoyl or unsubstituted or substituted carbamoyl; R₄ is hydrogen or 1-3 substituents selected from lower alkyl, lower alkoxy, halogen, cyano, carbalkoxy, alkanoyl, aroyl, arylazo, -SO₃-aryl, alkylsulfonyl, arylsulfonyl, unsubstituted or substituted carbamoyl, unsubstituted or substituted sulfamoyl, alkylthio, thiocyano, 2-cyanoethylthio, 2-cyanoethylsulfonyl, or alkanoylamino; R₅ is hydrogen or a group selected from lower alkyl, cycloalkyl, aryl, alkylthio, arylthio, cyanomethylthio, halogen, alkysulfonyl, arylsulfonyl, lower alkoxy, benzylthio, allylthio, unsubstituted or substituted sulfamoyl, thiocyano or alkanoylamino; R₆ is hydrogen or a group selected from lower alkyl, aryl, alkylthio, alkylsulfonyl, halogen, cyano, 2-carbalkoxyethylthio or benzylthio; R₇ is hydrogen or 1-2 substituents selected from lower alkyl, halogen, nitro, lower carbalkoxy, cyano, alkylthio, 2-hydroxyethylthio, arylthio, alkylsulfonyl or arylsulfonyl; R₈ is hydrogen or a group selected from lower alkyl, lower alkoxy, nitro, halogen or unsubstituted or substituted sulfamoyl; R₉ is 1-3 substituents selected from lower alkyl, aryl, cyano, lower carbalkoxy, cyclohexylcarbonyl, alkanoyl, aroyl, halogen, formyl, unsubstituted or substituted carbamoyl, thiocyano, alkysulfonyl, arylsulfonyl, unsubstituted or substituted sulfamoyl, nitro, arylazo or cinnamoyl; R₁₀ is hydrogen or 1-3 substituents selected from lower alkyl, halogen, lower alkoxy, lower alkylsulfonyl, arylsulfonyl, carbalkoxy, aryl, unsubstituted or substituted carbamoyl; unsubstituted or substituted sulfamoyl, formyl, or thiocyano; R₁₁ is hydrogen, cycloalkyl, lower alkyl, aryl, alkylsulfonyl, or arylsulfonyl; R₁₂ is hydrogen or 1-2 substituents selected from lower alkyl, aryl, cyano, nitro, lower carbalkoxy, carbamoyl, lower alkylthio, cyanomethyl; R₁₃ is hydrogen, lower alkyl, lower alkylthio, arylthio, carbalkoxy, halogen, lower alkylsulfonyl, or arylsulfonyl; R₁₄ is selected from hydrogen, unsubstituted or substituted alkyl, aryl, cycloalkyl, or allyl; and R₁₅ is hydrogen or 1-2 substituents selected from lower alkyl, lower alkoxy, halogen, nitro, cyano, alkylthio, arylthio, alkylsulfonyl, arylsulfonyl or aryloxy.

Claim 20

A compound according to claim 1 having the formula 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-thiadiazol-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 the residue of an electron rich aromatic carbocyclic or heterocyclic coupling component, and wherein at least one -Z is present.

Claim 21

A compound according to claim 20 wherein D is selected from wherein: R₃ is hydrogen or 1-2 substituents selected from lower alkyl, aryl, arylazo, halogen, cyano, formyl, carbalkoxy, nitro, thiocyano, lower alkylsulfonyl, arylsulfonyl, trifluoromethyl, alkanoyl, aroyl, unsubstituted or substituted sulfamoyl or unsubstituted or substituted carbamoyl; R₄ is hydrogen or 1-3 substituents selected from lower alkyl, lower alkoxy, halogen, cyano, carbalkoxy, alkanoyl, aroyl, arylazo, -SO₃-aryl, alkylsulfonyl, arylsulfonyl, unsubstituted or substituted carbamoyl, unsubstituted or substituted sulfamoyl, alkylthio, thiocyano, 2-cyanoethylthio, 2-cyanoethylsulfonyl, or alkanoylamino; R₅ is hydrogen or a group selected from lower alkyl, cycloalkyl, aryl, alkylthio, arylthio, cyanomethylthio, halogen, alkysulfonyl, arylsulfonyl, lower alkoxy, benzylthio, allylthio, unsubstituted or substituted sulfamoyl, thiocyano or alkanoylamino; R₆ is hydrogen or a group selected from lower alkyl, aryl, alkylthio, alkylsulfonyl, halogen, cyano, 2-carbalkoxyethylthio or benzylthio; R₇ is hydrogen or 1-2 substituents selected from lower alkyl, halogen, nitro, lower carbalkoxy, cyano, alkylthio, 2-hydroxyethylthio, arylthio, alkylsulfonyl or arylsulfonyl; R₈ is hydrogen or a group selected from lower alkyl, lower alkoxy, nitro, halogen or unsubstituted or substituted sulfamoyl; R₁₀ is hydrogen or 1-3 substituents selected from lower alkyl, halogen, lower alkoxy, lower alkylsulfonyl, arylsulfonyl, carbalkoxy, aryl, unsubstituted or substituted carbamoyl; unsubstituted or substituted sulfamoyl, formyl, or thiocyano; R₁₁ is hydrogen, lower alkyl, cycloalkyl, aryl, alkylsulfonyl, or arylsulfonyl; R₁₂ is hydrogen or 1-2 substituents selected from lower alkyl, aryl, cyano, lower carbalkoxy, nitro, carbamoyl, lower alkylthio, cyanomethyl; R₁₃ is hydrogen, lower alkyl, lower thioalkyl, arylthio, carbalkoxy, halogen, lower alkylsulfonyl, or arylsulfonyl; R₃₄ is selected from lower alkenyl, lower alkyl, optionally substituted benzyl, hydroxyalkyl, carbamoylalkyl, -alkylene-CO₂⁻M⁺ or -alkylene-SO₃⁻M⁺; wherein M⁺ is H⁺, Na⁺, K⁺, Li⁺ or NH₄⁺; and wherein X⁻ is a counter anion selected from Cl⁻, Br⁻, CH₃SO₄⁻, C₂H₅SO₄⁻, ZnCl₄⁻²/2; wherein at least one poly(oxyalkylene) moiety Z is present.

Claim 22

A compound according to any one of claims 10, 11, 12, 15, 16, 17, 18, or 20 wherein Ar is the residue of a reactant 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.

Claim 23

A compound according to any one of claims 10, 12, 15, 16, 17, 18, or 20 wherein Ar is selected from the radicals wherein: R₁₆ is hydrogen or 1-2 substituents selected from lower alkyl, trifluoromethyl, lower alkoxy, arylthio, aryloxy, halogen, -CH₂-O-Z or -O-alkylene-Z; R₁₇ and R₁₈ are each independently selected from -Z, straight or branched lower alkenyl; cycloalkyl; cycloalkyl substituted with hydroxy, alkoxy, alkyl, halogen or alkanoyloxy; phenyl; phenyl substituted with one or more groups selected from lower alkyl, lower alkoxy, cyano, alkanoyloxy or -L-Z; straight or branched chain alkyl of 1-12 carbons and such alkyl substituted with one or more of cyano, halogen, 2-pyrrolidino, phthalimidino, vinylsulfonyl, acrylamido, o-benzoic sulfonimido, a group of the formula phenyl, and phenyl substituted with lower alkyl, lower alkoxy, halogen, carbalkoxy, cyano, carboxy or acyloxy; R₁₉ is selected from hydrogen, lower alkyl, or lower alkanoylamino, lower alkoxy, halogen; R₂₀ is selected from hydrogen; lower alkyl; lower alkyl substituted with hydroxy, acyloxy, phenyl, cycloalkyl, halogen or alkoxy; cycloalkyl; phenyl; phenyl substituted with lower alkyl, lower alkoxy, halogen, hydroxy, alkanoylamino, carbalkoxy, carboxy, cyano, or alkanoyloxy; W is selected from: lower alkylene of 1-3 carbons; lower alkylene substituted with hydroxy, halogen, alkoxy or acyloxy; vinyl; 1,2-phenylene; 1,2-phenylene substituted with lower alkyl, lower alkoxy halogen, carboxy or carbalkoxy; 1,2-cyclohexylene; -O-CH₂-; -CH₂OCH₂-; -SCH₂-; -N(R₂₁)CH₂-; -N(R₂₁)CH₂CH₂-; or -CH₂N(R₂₁)CH₂-; wherein the alkyl group represented by R₁₇ and R₁₈ can be further substituted with a groups selected from those of the formulae: -O-R₂₁; -SO₂-R₂₂; -CON(R₂₁)R₂₃; -SO₂N(R₂₁)R₂₃; -N(R₂₁)SO₂R₂₂; -OCO-R₂₃; -OCO₂R₂₃; -OCON(R₂₁)R₂₃; -SR₂₄ or -SO₂CH₂CH₂SR₂₄; wherein R₂₁ and R₂₃ are selected from hydrogen; lower alkyl; lower alkyl substituted with hydroxy, aryloxy, halogen, cycloalkyl or phenyl; cycloalkyl; phenyl; phenyl substituted with lower alkyl, lower alkoxy, halogen, hydroxy, alkanoylamino, carbalkoxy, carboxy, cyano or alkanoyloxy; R₂₂ represents the same substituents listed for R₂₁ and R₂₃ excepting hydrogen; R₂₄ is selected from a group listed above for R₂₁ and R₂₃ plus benzothiazol-2-yl, benzimidazol-2-yl, pyridyl, pyrimidinyl, 1,3,4-thiadiazolyl, 1,3,4-oxadiazolyl, naphthyl or triazolyl; R₂₅, R₂₆, and R₂₇ are independently selected from hydrogen or lower alkyl; R₂₈ is hydrogen, cycloalkyl, alkyl, 2-thienyl, phenyl, phenyl substituted with halogen, lower alkyl, or lower alkoxy; R₂₉ is hydrogen or 1-2 substituents selected from lower alkyl, lower alkoxy or halogen; R₃₀ is selected from cyano, carbalkoxy, alkylsulfonyl, arylsulfonyl or unsubstituted or substituted carbamoyl; R₃₁ is hydrogen, lower alkyl or aryl; R₃₂ and R₃₃ are independently selected from hydrogen, lower alkyl, lower alkoxy, halogen or -Z; wherein X is a covalent bond, oxygen, or sulfur; and L is selected from X or -SO₂-, -SO₂N(R₂₁)-, -COO-, -N(SO₂R₂₂)- or -N(R₂₁)-; and with the proviso that the compound contain at least one -Z moiety.

Claim 24

A methine compound according to claim 15 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 M is an active methylene residue selected from those of the formulae wherein: R₃₅ is selected from cyano, -CON(R₃₆)R₃₇, -CO₂R₃₆, -COR₃₈, or -SO₂R₃₈; R₃₆ and R₃₇ are selected from hydrogen, cycloalkyl, unsubstituted or substituted alkyl, phenyl, phenyl substituted with lower alkyl, lower alkoxy, halogen cyano or nitro; R₃₈ is selected from substituents represented by R₃₆ and R₃₇ excepting hydrogen; R₃₉ is selected from lower alkyl, cycloalkyl or aryl; R₄₀ is selected from hydrogen, alkyl or aryl; R₄₁ is selected from hydrogen, lower alkyl, aryl or carbalkoxy; R₄₂ is hydrogen or 1-2 substituents selected from lower alkyl, lower alkoxy or halogen; R₄₃ is selected from: lower alkenyl, lower alkyl, optionally substituted benzyl, hydroxyalkyl, carbamoylalkyl, -alkylene-CO₂⁻M⁺ or -alkylene-SO₃⁻M⁺; M⁺ is H⁺, Na⁺, K⁺, Li⁺ or NH₄⁺; X⁻ is a counter anion selected from Cl⁻, Br⁻, CH₃SO₄⁻, C₂H₅SO₄⁻, ZnCl₄⁻²/2; and R₄₄ is optionally substituted aryl.

Claim 25

A compound according to claim 16 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 M is an active methylene residue selected from those of the formulae wherein: R₃₅ is selected from cyano, -CON(R₃₆)R₃₇, -CO₂R₃₆, -COR₃₈, -SO₂R₃₈ or -CONHCONH₂; R₃₆ and R₃₇ are selected from hydrogen, cycloalkyl, unsubstituted or substituted alkyl, phenyl, phenyl substituted with lower alkyl, lower alkoxy, halogen cyano or nitro; R₃₈ is selected from substituents represented by R₃₆ and R₃₇ excepting hydrogen; R₃₉ is selected from lower alkyl, cycloalkyl or aryl; R₄₀ is selected from hydrogen, alkyl or aryl; R₄₁ is selected from hydrogen, lower alkyl, aryl or carbalkoxy; R₄₂ is hydrogen or 1-2 substituents selected from lower alkyl, lower alkoxy or halogen; and R₄₄ is optionally substituted aryl.