US4169203A
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Water-soluble polymeric colorants containing anionic water-solubilizing groups
Assignee: Dynapol Shareholders Liquidating Trust
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Filing: 1976-11-18
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Granted: 1979-09-25
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Expires: 1996-11-18
Abstract
Abstract Acetylation of residual primary and secondary alkyl amine groups present in the structure of polymeric colorants and the acetylated colorant products are disclosed. The acetylation is a post production step. The acetylation improves the colorants' water solubility.
Inventors
- 👤 Robert E. Wingard
- 👤 Daniel J. Dawson
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 20:24
CPC Classifications
C; C09; C09B; C09B69/00; C09B69/10; Y; Y10; Y10S; Y10S534/00; Y10S534/03
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
113 words
A water-soluble polymeric colorant containing anionic water-solubilizing groups selected from the group consisting of sulfonate groups, carboxylate groups, sulfamate groups and phosphonate groups; and comprising a nonchromophoric organic polymer backbone to which is covalently bonded a plurality of units of organic chromophore and a plurality of residual primary or secondary alkyl nitrogens, the number of said residual primary or secondary alkyl nitrogens present in an acetylated form as amides being at least twice the number of said residual primary or secondary alkyl nitrogens present as unacetylated amines and the number of anionic water-solubilizing groups being at least three times the number of said residual primary or secondary alkyl nitrogens present as unacetylated amines.
Claim 2
Dependent Claim
113 words
A water-soluble polymeric colorant containing anionic water-solubilizing groups selected from the group consisting of sulfonate groups, carboxylate groups, sulfamate groups and phosphonate groups; and comprising a nonchromophoric organic polymer backbone to which is covalently bonded a plurality of units of organic chromophore and a plurality of residual primary or secondary alkyl nitrogens, the number of said residual primary or secondary alkyl nitrogens present in an acetylated form as amides being at least twice the number of said residual primary or secondary alkyl nitrogens present as unacetylated amines and the number of anionic water-solubilizing groups being at least three times the number of said residual primary or secondary alkyl nitrogens present as unacetylated amines.
Claim 3
Dependent Claim
15 words
The water-soluble polymeric colorant of claim 1, wherein the anionic water-solubilizing groups are sulfonate groups.
Claim 4
Dependent Claim
88 words
A water-soluble polymeric colorant of the formula ##STR34## Wherein R is hydrogen, or a lower alkyl, Chrom is an organic optically chromophoric group attached via an aromatic carbon atom in its structure directly to NR, M + is an ammonium or alkali metal cation, A equals from 0.1 to 2.0 times B+D, B equals from 2 to 20 times D, and E equals at least 3 times D, and from 0.3 to about 1 times A+B+D and the sum of A+B+D+E is a number from 100 to 10,000.
Claim 5
Dependent Claim
88 words
A water-soluble polymeric colorant of the formula ##STR34## Wherein R is hydrogen, or a lower alkyl, Chrom is an organic optically chromophoric group attached via an aromatic carbon atom in its structure directly to NR, M + is an ammonium or alkali metal cation, A equals from 0.1 to 2.0 times B+D, B equals from 2 to 20 times D, and E equals at least 3 times D, and from 0.3 to about 1 times A+B+D and the sum of A+B+D+E is a number from 100 to 10,000.
Claim 6
Dependent Claim
10 words
The polymeric colorant of claim 3 wherein R is hydrogen.
Claim 7
Dependent Claim
68 words
The polymeric colorant of claim 4 wherein Chrom is an anthrapyridone optical chromophore of the structure ##STR35## wherein R 1 is selected from among hydrogen, a 1 to 4 carbon alkyl and a 6 carbon aryl, R 2 is selected from among a 6 carbon aryl and 1 to 4 carbon alkyls and alkoxies and R 3 is selected from among hydrogen and 1 to 4 carbon alkyls.
Claim 8
Dependent Claim
29 words
The polymeric colorant of claim 5 wherein A+b+d+e equals from 300 to 2000 A equals from 0.1 to 1 times B+D B equals from 3 to 20 times D.
Claim 9
Dependent Claim
43 words
The polymeric colorant of claim 6 wherein A+b+d+e equals from about 500 to about 1500 A equals from about 0.3 to 0.7 times B+D B equals from about 6 to about 200 times D, and E equals about 0.4 to 0.6 times A+B+D
Claim 10
Dependent Claim
12 words
The polymeric colorant of claim 7 wherein Chrom has the structure ##STR36##
Claim 11
Dependent Claim
12 words
The polymeric colorant of claim 7 wherein Chrom has the structure ##STR37##
Claim 12
Dependent Claim
85 words
A water-soluble polymeric colorant of the formula ##STR38## wherein Chrom is an organic optically chromophoric group attached to NR via an aromatic carbon atom present in Chrom's covalent structure, R is hydrogen, methyl or ethyl, M + is an ammonium ion or an alkali metal cation and A+b+d+e equals from 100 to 10,000 A equals from 0.1 to 20 times B+D, B equals from 2 to 20 times D, and E equals at least 3 times D and from 0.3 to about 1 times A+B+D.
Claim 13
Dependent Claim
85 words
A water-soluble polymeric colorant of the formula ##STR38## wherein Chrom is an organic optically chromophoric group attached to NR via an aromatic carbon atom present in Chrom's covalent structure, R is hydrogen, methyl or ethyl, M + is an ammonium ion or an alkali metal cation and A+b+d+e equals from 100 to 10,000 A equals from 0.1 to 20 times B+D, B equals from 2 to 20 times D, and E equals at least 3 times D and from 0.3 to about 1 times A+B+D.
Claim 14
Dependent Claim
13 words
The polymeric colorant of claim 10 wherein Chrom is an anthraquinone optical chromophore.
Claim 15
Dependent Claim
29 words
The polymeric colorant of claim 11 wherein A+b+d+e equals from 300 to 2000 A equals from 0.1 to 1 times B+D B equals from 3 to 20 times D.
Claim 16
Dependent Claim
42 words
The polymeric colorant of claim 12 A+b+c+d equals from about 500 to about 1500 A equals from about 0.3 to 0.7 times B+D B equals from about 6 to about 200 times D, and E equals about 0.4 to 0.6 times A+B+D.
Claim 17
Dependent Claim
10 words
The polymeric colorant of claim 13 wherein R is hydrogen.
Claim 18
Dependent Claim
12 words
The polymeric colorant of claim 14 wherein Chrom has the structure ##STR39##
Claim 19
Dependent Claim
12 words
The polymeric colorant of claim 14 wherein Chrom has the structure ##STR40##
Claim 20
Dependent Claim
116 words
A water soluble polymeric colorant of a formula selected from: ##STR41## wherein R 1 is a 2 to 6 carbon alkyl or alkyl sulfonate group, Chrom is an optically chromophoric group covalently bonded to R 1 through an aromatic carbon, Anon is an anionic solubilizer group selected from among ##STR42## wherein M + is ammonium or an alkali metal cation, and A, A', B, D and E are numbers defined as follows: A+a'+b+d+e equals from 100 to 10,000, A+a' equals from 0.1 to 2.0 times B+D, A equals from 1 to 20 times A', B equals from 2 to 20 times D, E equals at least 3 times A'+D, and from 0.3 to 1 times A+A'+B+D.
Claim 21
Dependent Claim
116 words
A water soluble polymeric colorant of a formula selected from: ##STR41## wherein R 1 is a 2 to 6 carbon alkyl or alkyl sulfonate group, Chrom is an optically chromophoric group covalently bonded to R 1 through an aromatic carbon, Anon is an anionic solubilizer group selected from among ##STR42## wherein M + is ammonium or an alkali metal cation, and A, A', B, D and E are numbers defined as follows: A+a'+b+d+e equals from 100 to 10,000, A+a' equals from 0.1 to 2.0 times B+D, A equals from 1 to 20 times A', B equals from 2 to 20 times D, E equals at least 3 times A'+D, and from 0.3 to 1 times A+A'+B+D.
Claim 22
Dependent Claim
13 words
The polymeric colorant of claim 17 wherein R 1 is a propyl sulfonate.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1982-09-24 | 1983-03-26 | 1983-09-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1986-09-24 | 1987-03-26 | 1987-09-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1990-09-24 | 1991-03-26 | 1991-09-25 | $7700.00 | Window Closed / Lapsed |