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Copolymers of dyes and acrylamide

Assignee: Produits Chimiques Ugine Kuhlmann
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Filing: 1977-01-25
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Granted: 1979-01-02
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Expires: 1997-01-25
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Abstract

Abstract Copolymers of acrylamide and dyes useful as reactive prepolymers for the preparation of structurally dyed water-insoluble macromolecular materials. The dyes have a polymerizable double bond, such as maleimido, acryloylamino or cyanovinyl groups.

Inventors

  • 👤 Michel M. L. Champenois

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-10-25 11:41
CPC Classifications
C; C09; C09B; C09B69/00; C09B69/10; C09B69/101; C08; C08F; C08F220/00; C08F220/02; C08F220/52; C08F220/54; C08F220/56; C09B1/00; C09B1/16; C09B1/20; C09B1/26; C09B1/32; C09B5/00; C09B5/02; C09B5/04

Claims Analysis

Total Claims: 4
Claim 1
Independent Claim 262 words
A structurally dyed, water insoluble, macromolecular material containing in copolymerized form, acrylamide, at least one azo, anthraquinone, pyrazolanthrone or phthalocyanine dye having at least one group of the formula: ##STR11## wherein R 1 is hydrogen or alkyl having 1 to 4 carbon atoms, R 2 is hydrogen, halogen, cyano, carboxy, carbonamido or alkoxycarbonyl with 1 to 4 carbons in the alkoxy chain, said groups being attached to a cyclic carbon atom of an aromatic nucleus of the dye molecule either directly or through an oxygen or sulfur atom or a ##STR12## R 3 being hydrogen or alkyl with 1 to 4 carbon atoms, at least one colorless base monomer selected from the group consisting of: styrene and its substituted derivatives, divinylbenzene, polybutadiene oligomers having vinyl groups, acrylic, methacrylic, crotonic, chloroacrylic, maleic, and itaconic acids and their anhydrides, nitriles, esters, amides, N-monoalkyl amides and N-dialkylamides, ethyleneglycol diacrylate, methylene-bis-acrylamide and methylene-bis-methacrylamide, vinyl esters of saturated carboxylic acids, vinyl halides and vinylidene halides, vinylpyridines, vinylpyrrolidines, vinylquinolines, and N-vinyl-imidazole, N-vinyl-carbazole, N-vinyl-pyrolidones of N-vinyl-caprolactam, obtained by first copolymerizing for 30 seconds to 5 minutes, in an aqueous medium and at a temperature from 0° C. to 100° C., in the presence of a tetravalent cerium complex as initiator, the dye with the acrylamide to form a reactive prepolymer, and then reacting in situ said prepolymers with the base monomer and the remaining free dye and acrylamide, the amount of dye being from 0.1 to 25% by weight of the base monomer and the amount of acrylamide being from 0.5 to 50% by weight of the base monomer.
Claim 2
Dependent Claim 262 words
A structurally dyed, water insoluble, macromolecular material containing in copolymerized form, acrylamide, at least one azo, anthraquinone, pyrazolanthrone or phthalocyanine dye having at least one group of the formula: ##STR11## wherein R 1 is hydrogen or alkyl having 1 to 4 carbon atoms, R 2 is hydrogen, halogen, cyano, carboxy, carbonamido or alkoxycarbonyl with 1 to 4 carbons in the alkoxy chain, said groups being attached to a cyclic carbon atom of an aromatic nucleus of the dye molecule either directly or through an oxygen or sulfur atom or a ##STR12## R 3 being hydrogen or alkyl with 1 to 4 carbon atoms, at least one colorless base monomer selected from the group consisting of: styrene and its substituted derivatives, divinylbenzene, polybutadiene oligomers having vinyl groups, acrylic, methacrylic, crotonic, chloroacrylic, maleic, and itaconic acids and their anhydrides, nitriles, esters, amides, N-monoalkyl amides and N-dialkylamides, ethyleneglycol diacrylate, methylene-bis-acrylamide and methylene-bis-methacrylamide, vinyl esters of saturated carboxylic acids, vinyl halides and vinylidene halides, vinylpyridines, vinylpyrrolidines, vinylquinolines, and N-vinyl-imidazole, N-vinyl-carbazole, N-vinyl-pyrolidones of N-vinyl-caprolactam, obtained by first copolymerizing for 30 seconds to 5 minutes, in an aqueous medium and at a temperature from 0° C. to 100° C., in the presence of a tetravalent cerium complex as initiator, the dye with the acrylamide to form a reactive prepolymer, and then reacting in situ said prepolymers with the base monomer and the remaining free dye and acrylamide, the amount of dye being from 0.1 to 25% by weight of the base monomer and the amount of acrylamide being from 0.5 to 50% by weight of the base monomer.
Claim 3
Dependent Claim 49 words
A structurally dyed macromolecular material as defined in claim 1 wherein said dye is an anthraquinone dye of the general formula: ##STR13## wherein Y represents hydrogen or sulfo, X represents hydrogen or chlorine, n represents 0 or 1, and the cyanovinyl group is in position 3, 4 or 5.
Claim 4
Dependent Claim 63 words
A structurally dyed macromolecular material as defined in claim 1 wherein said dye is a pyrazolanthrone dye of the general formula: ##STR14## wherein X, X', X" represents hydrogen or halogen, Z represents hydrogen, lower alkyl or benzamido, the cyanovinyl is in position 3, 4 or 5, A represents hydrogen, halogen or lower alkyl, A' represents hydrogen, and Aa' may be a covalent bond.

References Cited (Backward Citations)

US2620324A Cited
US2805218A Cited
US2895967A Cited
US2976294A Cited
US3503087A Cited
US3637596A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1982-01-01 1982-07-03 1983-01-02 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1986-01-01 1986-07-03 1987-01-02 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1990-01-01 1990-07-03 1991-01-02 $7700.00 Window Closed / Lapsed

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