US4111648A
Expired / Lapsed
US
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Reactive dyeing systems using dyes with carboxylic acid groups
Assignee: Burlington Industries Inc
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Filing: 1977-02-28
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Granted: 1978-09-05
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Expires: 1997-02-28
Abstract
Abstract Carboxy substituted aromatic chromophores are reactively linked to fibers containing alcoholic hydroxyl groups, amino groups or thiol groups, such as cellulosic fibers, with the linkage produced in the presence of a cyanamide compound, such as cyanamide or dicyandiamide.
Inventors
- 👤 Bobby Lee McConnell
- 👤 Raymond Thornton
- 👤 Louis Atkins Graham
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 02:46
CPC Classifications
D; D06; D06P; D06P3/00; D06P3/58; D06P3/60; D06P3/68; C; C09; C09B; C09B1/00; C09B1/16; C09B1/20; C09B1/26; C09B1/32; C09B1/34; C09B1/343; D06P1/00; D06P1/38; D06P1/44; D06P1/64; D06P1/642; D06P5/00; D06P5/02; Y; Y10; Y10S; Y10S8/00; Y10S8/916; Y10S8/918; Y10S8/92; Y10S8/924
Claims Analysis
Total Claims: 20
Claim 1
Independent Claim
162 words
A method of forming a reactively dyed polymeric substrate, said method comprising (a) contacting a polymeric cellulosic substrate containing non-phenolic alcoholic active hydrogen atoms at a pH of about 1.5 to about 11 with (i) a cyanamide compound selected from the group consisting of cyanamide, alkyl-substituted cyanamide, dicyandiamide and alkyl-substituted dicyandiamide, wherein said alkyl groups each contain from 1 to 6 carbon atoms, and with (ii) a coloring amount of an aromatic dye of the formula Dye-COOH, wherein Dye is an aromatic chromophore wherein the ratio of equivalents of said cyanamide compound to each carboxylic acid function of said aromatic dye is at least about 2:1, and (b) heating the contacted substrate to a temperature of at least 200° F. for a time sufficient to fix said chromophore to said substrate by condensation reaction between said active hydrogen and the --COOH group of said dye so as to join the chromophore to the substrate through the C atom of said --COOH group.
Claim 2
Independent Claim
162 words
A method of forming a reactively dyed polymeric substrate, said method comprising (a) contacting a polymeric cellulosic substrate containing non-phenolic alcoholic active hydrogen atoms at a pH of about 1.5 to about 11 with (i) a cyanamide compound selected from the group consisting of cyanamide, alkyl-substituted cyanamide, dicyandiamide and alkyl-substituted dicyandiamide, wherein said alkyl groups each contain from 1 to 6 carbon atoms, and with (ii) a coloring amount of an aromatic dye of the formula Dye-COOH, wherein Dye is an aromatic chromophore wherein the ratio of equivalents of said cyanamide compound to each carboxylic acid function of said aromatic dye is at least about 2:1, and (b) heating the contacted substrate to a temperature of at least 200° F. for a time sufficient to fix said chromophore to said substrate by condensation reaction between said active hydrogen and the --COOH group of said dye so as to join the chromophore to the substrate through the C atom of said --COOH group.
Claim 3
Dependent Claim
12 words
Method according to claim 1, wherein said chromophore is an azo chromophore.
Claim 4
Dependent Claim
12 words
Method according to claim 1, wherein said chromophore is an anthraquinone chromophore.
Claim 5
Dependent Claim
17 words
Method according to claim 1, wherein said chromophore is substituted with a plurality of carboxylic acid substituents.
Claim 6
Dependent Claim
13 words
Method according to claim 4, wherein said chromophore contains two carboxylic acid substituents.
Claim 7
Dependent Claim
36 words
Method according to claim 1, wherein said carboxylic group is directly attached to a ring carbon atom of a phenyl group, and an amino group is attached to an adjacent carbon atom of the phenyl ring.
Claim 8
Dependent Claim
12 words
Method according to claim 1, wherein said substrate is a textile substrate.
Claim 9
Dependent Claim
19 words
Method according to claim 7, wherein said textile substrate is an organic polymer containing a plurality of hydroxyl groups.
Claim 10
Dependent Claim
11 words
Method according to claim 8, wherein said cyanamide compound is cyanamide.
Claim 11
Dependent Claim
11 words
Method according to claim 8, wherein said cyanamide compound is dicyandiamide.
Claim 12
Dependent Claim
12 words
Method according to claim 8, wherein said substrate is in fibrous form.
Claim 13
Dependent Claim
24 words
Method according to claim 1, wherein the chromophore is selected from the group consisting of anthraquinone, phthalocyanine, azo, benzanthrone, naphthaquinone, triarylmethane and cyanine chromophores.
Claim 14
Dependent Claim
31 words
A relatively dyed cellulosic textile substrate of the formula ##STR39## wherein Dye is an aromatic chromophore linked chemically to the carbonyl group, and R is the chain of the cellulose polymer.
Claim 15
Dependent Claim
31 words
A relatively dyed cellulosic textile substrate of the formula ##STR39## wherein Dye is an aromatic chromophore linked chemically to the carbonyl group, and R is the chain of the cellulose polymer.
Claim 16
Dependent Claim
26 words
The dyed substrate according to claim 13, wherein the chromophore is selected from the group consisting of anthraquinone, phthalocyanine, azo, benzanthrone, naphthaquinone, triarylmethane and cyanine chromophores.
Claim 17
Dependent Claim
121 words
A composition for reactively dyeing cellulosic textile substrates containing non-phenolic alcoholic substituents, said composition comprising an aqueous solution having a pH of from about 1.5 to about 11 and containing (a) at least 0.1% by weight of an aromatic dyestuff which is substituted by at least one carboxyl group which is reactive with active hydrogen atoms of said substituents so that the dyestuff can be joined to the substrate through the C atom of said --COOH group, and (b) a water soluble cyanamide compound selected from the group consisting of cyanamide, alkyl-substituted cyanamide, dicyandiamide and alkyl-substituted dicyandiamide, wherein the alkyl substituents contain from 1-6 carbon atoms, wherein the ratio equivalent of cyanamide compound to carboxylic acid is at least about 2:1.
Claim 18
Dependent Claim
121 words
A composition for reactively dyeing cellulosic textile substrates containing non-phenolic alcoholic substituents, said composition comprising an aqueous solution having a pH of from about 1.5 to about 11 and containing (a) at least 0.1% by weight of an aromatic dyestuff which is substituted by at least one carboxyl group which is reactive with active hydrogen atoms of said substituents so that the dyestuff can be joined to the substrate through the C atom of said --COOH group, and (b) a water soluble cyanamide compound selected from the group consisting of cyanamide, alkyl-substituted cyanamide, dicyandiamide and alkyl-substituted dicyandiamide, wherein the alkyl substituents contain from 1-6 carbon atoms, wherein the ratio equivalent of cyanamide compound to carboxylic acid is at least about 2:1.
Claim 19
Dependent Claim
32 words
Composition according to claim 15, wherein said dye has the formula: ##STR40## wherein R' D is the remaining part of a dye and is singly or doubly attached to the aminocarboxyphenyl ring.
Claim 20
Dependent Claim
21 words
A method according to claim 1, wherein the contacted substrate of step (a) is dried prior to heating in step (b).
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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) | 1981-09-04 | 1982-03-06 | 1982-09-05 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-04 | 1986-03-06 | 1986-09-05 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-04 | 1990-03-06 | 1990-09-05 | $7700.00 | Window Closed / Lapsed |