Polymeric triarylmethane dyes
AssigneeMinnesota Mining and Manufacturing Company
InventorSmarajit Mitra
Life of this patent
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Abstract
Polymeric and copolymeric aminotriarylmethane dyes having polyester, polyethyleneimine, or polyurethane backbones, and a process for their preparation, are disclosed. The novel dyes are highly colored and resistant to leaching by solvents.
Claims14
A polymeric aminotriarylmethane dye having a polyester, polycarbonate, polyethyleneimine or polyurethane backbone, said dye comprising repeating units selected from the group consisting of ##STR37## wherein R, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X, a, and b are as defined below, and said dye having at least one arylamino unit of the general formula:
- ##STR38## wherein a and b are independently zero or an integer of 1 to 3;
- X is oxygen or sulfur;
- Y is oxygen or --NH--;
- R is a divalent organic group selected from (1) aliphatic groups having 2 to 12 carbon atoms and up to 2 non-contiguous catenary groups selected from --O--, --S--, and --NR.sup.1 --, in which R.sup.1 is a lower alkyl group having one to four carbon atoms, (2) cycloaliphatic groups having 5 12 carbon atoms, and (3) arylene groups having 6 to 12 carbon atoms;
- c, d, and e are independently zero or one, with the provisos that when e is zero, then a is zero, and when c is zero or Y is oxygen, then X is oxygen;
- R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are independently hydrogen, and auxochromic group, a bathochromic group or R.sup.2 and R.sup.3 or R.sup.4 and R.sup.5 together are a benzo group;
- Ar.sup.1 and Ar.sup.2 are independently aromatic groups having one or two 5- or 6-atom rings with conjugated unsaturation, the 5-atom rings having four carbon atoms and one of oxygen, sulfur, or nitrogen or three carbon atoms, one nitrogen, and one of oxygen or sulfur in the 1,3-position or nitrogen in the 1,2- or 1,3-position, the 6-atom rings having six carbon atoms or five carbon atoms and one nitrogen, or four carbon atoms and two nitrogens in the 1,2-1,3-, or 1,4-position or three carbon atoms and three nitrogens in the 1,3,5-position;
- and
- W is a divalent group selected from the group consisting of a coordinate bond, --O--, --S--, ##STR39## hydrogen or lower alkyl group having one to four atoms and R.sup.7 and R.sup.8 are independently hydrogen or a lower alkyl group having one to four carbon atoms;
- f is zero or one;
- and
- Z.crclbar. is an anion.
A polymeric or copolymeric aminotriarylmethane dye having a polyester, polycarbonate, or polyurethane backbone, said dye comprising repeating units selected from the group consisting of ##STR40## wherein R, R.sup.2, R.sup.3, R.sup.4, R.sup.5, X, a, and b are as defined below, and said dye having 0.1 to 100 mol percent of arylamino units of the general formula:
- ##STR41## wherein a and b are independently zero or an integer of 1 to 3;
- X is oxygen or sulfur;
- Y is oxygen or --NH--;
- R is a divalent organic group selected from (1) aliphatic groups having 2 to 12 carbon atoms and up to 2 non-contiguous catenary groups selected from --O--, --S--, and --NR.sup.1 --, in which R.sup.1 is a lower alkyl group having one to four carbon atoms, (2) cycloaliphatic groups having 5 to 12 carbon atoms, and (3) arylene groups having 6 to 12 carbon atoms;
- c and d are independently zero or one, with the proviso that when c is zero or Y is oxygen, then X is oxygen;
- R.sup.2, R.sup.3, R.sup.4, and R.sup.5 are independently hydrogen, an auxochromic group, a bathochromic group or R.sup.2 and R.sup.3 or R.sup.4 and R.sup.5 together are a benzo group;
- Ar.sup.1 and Ar.sup.2 are independently aromatic groups having one or two 5- or 6-atom rings with conjugated unsaturation, the 5-atom rings having four carbon atoms and one of oxygen, sulfur, or nitrogen or three carbon atoms, one nitrogen, and one of oxygen or sulfur in the 1,3-position or nitrogen in the 1,2- or 1,3-position, the 6-atom rings having six carbon atoms or five carbon atoms and one nitrogen, or four carbon atoms and two nitrogens in the 1,2-1,3-, or 1,4-position or three carbon atoms and three nitrogens in the 1,3,5-position;
- and
- W is a divalent group selected from the group consisting of a coordinate bond, --O--, --S--, ##STR42## in which R.sup.6 is hydrogen or lower alkyl group having one to four atoms and R.sup.7 and R.sup.8 are independently hydrogen or a lower alkyl group having one to four carbon atoms;
- f is zero or one;
- Z.crclbar. is an anion, and 99.9 to 0.0 mol percent of units of a non-arylamino unit-containing polyester or polyurethane having the general formula:
- ##STR43## in which R.sup.9 is an alkylene group having 2 to 12 carbon atoms or polyoxyethylene, polyoxypropylene or polyoxybutylene having a molecular weight up to 3000 and X, Y, R, c, and d are the same as defined above.
Dependencies are inferred from the claim text.