Polymeric triarylmethane dyes
First Claim
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1. 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, R2, R3, R4, R5, 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 --NR1 --, in which R1 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;
R2, R3, R4, and R5 are independently hydrogen, and auxochromic group, a bathochromic group or R2 and R3 or R4 and R5 together are a benzo group;
Ar1 and Ar2 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 R7 and R8 are independently hydrogen or a lower alkyl group having one to four carbon atoms;
f is zero or one; and
Z⊖
is an anion.
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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.
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Citations
14 Claims
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1. 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, R2, R3, R4, R5, 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 --NR1 --, in which R1 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; R2, R3, R4, and R5 are independently hydrogen, and auxochromic group, a bathochromic group or R2 and R3 or R4 and R5 together are a benzo group; Ar1 and Ar2 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 R7 and R8 are independently hydrogen or a lower alkyl group having one to four carbon atoms; f is zero or one; and Z⊖
is an anion. - View Dependent Claims (3, 4, 5, 6, 7, 8, 9, 10, 13, 14)
- ##STR38## wherein a and b are independently zero or an integer of 1 to 3;
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2. 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, R2, R3, R4, R5, 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 --NR1 --, in which R1 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; R2, R3, R4, and R5 are independently hydrogen, an auxochromic group, a bathochromic group or R2 and R3 or R4 and R5 together are a benzo group; Ar1 and Ar2 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 R6 is hydrogen or lower alkyl group having one to four atoms and R7 and R8 are independently hydrogen or a lower alkyl group having one to four carbon atoms; f is zero or one; Z⊖
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 R9 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. - View Dependent Claims (11, 12)
- ##STR41## wherein a and b are independently zero or an integer of 1 to 3;
Specification
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Current AssigneeMinnesota Mining and Manufacturing Co (3M Company)
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Original AssigneeMinnesota Mining and Manufacturing Co (3M Company)
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InventorsMitra, Smarajit
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Primary Examiner(s)Raymond, Richard L.
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Assistant Examiner(s)COVINGTON, RAYMOND K
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Application NumberUS06/336,637Time in Patent Office1,016 DaysField of Search260/386, 260/389, 260/390, 260/351, 260/365, 260/369, 260/367, 260/346.72, 260/347.7, 260/343.44, 260/239 BF, 260/239.3 R, 260/236, 260/317, 548/425, 548/536, 548/146, 548/152, 548/217, 548/333, 548/215, 548/335, 548/325US Class Current525/437CPC Class CodesC08G 18/329 containing aromatic groupsC08G 18/831 by oxygen-containing compou...C08G 63/6856 Dicarboxylic acids and dihy...C08G 73/02 Polyamines
