Poly(oxyalkylene) substituted xanthene colorant and method for making the same

Claim 1

A xanthene colorant comprising a compound having the structure: ##STR11## where Y is a poly(oxyalkylene) substituent having a straight or branched polymer chain of from 3 to 375 monomer units selected from ethylene oxide, propylene oxide, butylene oxide and glycidol; where R 1 and R 2 are independently selected from H, C1-C20 alkyl, aryl and Y, provided that if either R 1 or R 2 is Y, the other is not H; R 3 is selected from C1-C20 alkyl, aryl and Y; R 4 and R 5 are independently selected from H, C1-C4 alkyl, C1-C4 alkoxy, Cl, Br and I; X is selected from H, SO 3 --, CO 2 --, COOR 6 , Cl, Br and OH, and R 6 is C1-C8 alkyl or aryl; and each Z is independently selected from SO 3 --, CO 2 --, COOR 7 , Cl, Br and OH, and R 7 is C1-C8 alkyl or aryl, and n is 0, 1, 2, 3 or 4.

Claim 22

A method of manufacturing a poly(oxyalkylene) substituted xanthene colorant comprising the steps of: (a) providing an aqueous solution of a triphenyl methane colorant, having (i) a first phenyl group substituted with an amino group in a position para to a central carbon, said amino group further having first and second substituents identified as Y, which are characterized by a straight or branched poly(oxyalkylene) chain of from 3 to 200 monomer units selected from ethylene oxide, propylene oxide, butylene oxide and glycidol; said first phenyl group is also substituted with an alkoxy group in a position ortho to said central carbon, wherein said alkoxy group has 1 to 4 carbon atoms, said first phenyl group is optionally methyl or ethyl substituted; (ii) said triphenyl methane colorant further having a second phenyl group substituted with an amino group in a position para to said central carbon, said amino group further having first and second substituents selected from H, C1-C20 alkyl, aryl and Y, provided that if one of said substituents is Y, the other cannot be H; said second phenyl group is also substituted with an hydroxyl or alkoxy group in a position ortho to said central carbon, wherein said alkoxy group has 1 to 4 carbon atoms, said second phenyl group is optionally methyl or ethyl substituted; (iii) said triphenyl methane further having a third phenyl group which is optionally substituted with up to three groups selected from SO 3 --, CO 2 and COOR, where R is C 1-4 alkyl; (b) providing a pH of less than 7 is said solution; and (c) heating said solution to a temperature of 150° C. or greater, causing a ring closure reaction and formation of an ether linkage between said ortho positions on said first and second phenyl groups.

Claim 23

A method of manufacturing a poly(oxyalkylene) substituted xanthene colorant comprising the steps of: (a) providing an aqueous solution of a triphenyl methane colorant, having (i) a first phenyl group substituted with an amino group in a position para to a central carbon, said amino group further having first and second substituents identified as Y, which are characterized by a straight or branched poly(oxyalkylene) chain of from 3 to 200 monomer units selected from ethylene oxide, propylene oxide, butylene oxide and glycidol; said first phenyl group is also substituted with an alkoxy group in a position ortho to said central carbon, wherein said alkoxy group has 1 to 4 carbon atoms, said first phenyl group is optionally methyl or ethyl substituted; (ii) said triphenyl methane colorant further having a second phenyl group substituted with an amino group in a position para to said central carbon, said amino group further having first and second substituents selected from H, C1-C20 alkyl, aryl and Y, provided that if one of said substituents is Y, the other cannot be H; said second phenyl group is also substituted with an hydroxyl or alkoxy group in a position ortho to said central carbon, wherein said alkoxy group has 1 to 4 carbon atoms, said second phenyl group is optionally methyl or ethyl substituted; (iii) said triphenyl methane further having a third phenyl group which is optionally substituted with up to three groups selected from SO 3 --, CO 2 and COOR, where R is C 1-4 alkyl; (b) providing a pH of less than 7 is said solution; and (c) heating said solution to a temperature of 150° C. or greater, causing a ring closure reaction and formation of an ether linkage between said ortho positions on said first and second phenyl groups.