US4477635A
Expired / Lapsed
US
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Polymeric triarylmethane dyes
Assignee: 3M Co
•
Filing: 1982-01-04
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Granted: 1984-10-16
•
Expires: 2002-01-04
Abstract
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.
Inventors
- 👤 Smarajit Mitra
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-31 14:37
CPC Classifications
C; C08; C08G; C08G18/00; C08G18/06; C08G18/83; C08G18/831; C08G18/28; C08G18/30; C08G18/32; C08G18/3271; C08G18/329; C08G63/00; C08G63/68; C08G63/685; C08G63/6854; C08G63/6856; C08G73/00; C08G73/02
Claims Analysis
Total Claims: 16
Claim 1
Independent Claim
371 words
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 2 , R 3 , R 4 , R 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 1 --, in which R 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 2 , R 3 , R 4 , and R 5 are independently hydrogen, and auxochromic group, a bathochromic group or R 2 and R 3 or R 4 and R 5 together are a benzo group; Ar 1 and Ar 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 7 and R 8 are independently hydrogen or a lower alkyl group having one to four carbon atoms; f is zero or one; and Z⊖ is an anion.
Claim 2
Dependent Claim
371 words
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 2 , R 3 , R 4 , R 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 1 --, in which R 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 2 , R 3 , R 4 , and R 5 are independently hydrogen, and auxochromic group, a bathochromic group or R 2 and R 3 or R 4 and R 5 together are a benzo group; Ar 1 and Ar 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 7 and R 8 are independently hydrogen or a lower alkyl group having one to four carbon atoms; f is zero or one; and Z⊖ is an anion.
Claim 3
Dependent Claim
429 words
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 2 , R 3 , R 4 , R 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 1 --, in which R 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 2 , R 3 , R 4 , and R 5 are independently hydrogen, an auxochromic group, a bathochromic group or R 2 and R 3 or R 4 and R 5 together are a benzo group; Ar 1 and Ar 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 6 is hydrogen or lower alkyl group having one to four atoms and R 7 and R 8 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 R 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.
Claim 4
Dependent Claim
429 words
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 2 , R 3 , R 4 , R 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 1 --, in which R 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 2 , R 3 , R 4 , and R 5 are independently hydrogen, an auxochromic group, a bathochromic group or R 2 and R 3 or R 4 and R 5 together are a benzo group; Ar 1 and Ar 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 6 is hydrogen or lower alkyl group having one to four atoms and R 7 and R 8 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 R 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.
Claim 5
Dependent Claim
17 words
The polymeric dye according to claim 1 wherein R contains one catenary --O--, --S--, or ##STR44## group.
Claim 6
Dependent Claim
32 words
The polymeric dye according to claim 1 wherein when R 2 and R 3 or R 4 and R 5 is a benzo group which is substituted by auxochromic or bathochromic groups.
Claim 7
Dependent Claim
23 words
The polymeric dye according to claim 1 wherein Ar 1 and Ar 2 are substituted by at least one auxochromic or bathochromic group.
Claim 8
Dependent Claim
17 words
The polymeric dye according to claim 1 having at least one unit of the general formula: ##STR45##
Claim 9
Dependent Claim
17 words
The polymeric dye according to claim 1 having at least one unit of the general formula: ##STR46##
Claim 10
Dependent Claim
17 words
The polymeric dye according to claim 1 having at least one unit of the general formula: ##STR47##
Claim 11
Dependent Claim
17 words
The polymeric dye according to claim 1 having at least one unit of the general formula: ##STR48##
Claim 12
Dependent Claim
17 words
The polymeric dye according to claim 1 having at least one unit of the general formula: ##STR49##
Claim 13
Dependent Claim
17 words
The polymeric dye according to claim 2 having at least one unit of the general formula: ##STR50##
Claim 14
Dependent Claim
17 words
The polymeric dye according to claim 2 having at least one unit of the general formula: ##STR51##
Claim 15
Dependent Claim
19 words
Resins comprising in the range of 0.001 to 10 weight percent of the polymeric dye according to claim 1.
Claim 16
Dependent Claim
26 words
The polymeric aminotriarylmethane dye according to claim 1 wherein f is zero and Ar 1 and Ar 2 are 6-atom aromatic rings containing only carbon atoms.
References Cited (Backward Citations)
US2816900A
Cited
US4353833A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1987-10-16 | 1988-04-16 | 1988-10-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1991-10-16 | 1992-04-16 | 1992-10-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1995-10-16 | 1996-04-16 | 1996-10-16 | $7700.00 | Window Closed / Lapsed |