GB725353A - Improvements in the dyeing of textile materials of an organic derivative of cellulose - Google Patents

Improvements in the dyeing of textile materials of an organic derivative of cellulose

Info

Publication number
GB725353A
GB725353A GB8358/53A GB835853A GB725353A GB 725353 A GB725353 A GB 725353A GB 8358/53 A GB8358/53 A GB 8358/53A GB 835853 A GB835853 A GB 835853A GB 725353 A GB725353 A GB 725353A
Authority
GB
United Kingdom
Prior art keywords
cyanoethyl
diaminodicyclohexylmethane
compound
mols
cyanobutyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired
Application number
GB8358/53A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB725353A publication Critical patent/GB725353A/en
Expired legal-status Critical Current

Links

Classifications

    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/645—Aliphatic, araliphatic or cycloaliphatic compounds containing amino groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/62—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds with sulfate, sulfonate, sulfenic or sulfinic groups
    • D06P1/628—Compounds containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6421—Compounds containing nitrile groups
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/6426—Heterocyclic compounds
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
    • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
    • D06P1/64—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing low-molecular-weight organic compounds without sulfate or sulfonate groups
    • D06P1/642—Compounds containing nitrogen
    • D06P1/649—Compounds containing carbonamide, thiocarbonamide or guanyl groups
    • D06P1/6492—(Thio)urethanes; (Di)(thio)carbamic acid derivatives; Thiuramdisulfide
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/401—Cellulose acetate using acid dyes
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
    • D06P3/34—Material containing ester groups
    • D06P3/40—Cellulose acetate
    • D06P3/405—Cellulose acetate using metallisable or mordant dyes

Abstract

Dyeings on textile materials containing organic derivatives of cellulose, e.g. cellulose acetate and ethyl cellulose, are rendered fast to acid-fading by impregnating the materials, before, during or after dyeing, with a colourless water-insoluble, fully saturated from 3 to 7-membered mononitrogen heterocyclic compound or an amino compound having in its molecule cycloaliphatic radicals, the compound in either case having attached to nitrogen at least one cyanoalkyl group of from 1 to 10 carbon atoms. The acid-fading inhibitor may be applied as an aqueous dispersion or, in the form of its formaldehydebisulphite compound, as an aqueous solution, and it may also be incorporated in the spinning mass from which the fibres are produced. Examples of specified acid-fading inhibitors are N - (o - cyano - ethyl) - spirocyclohexylethyleneimine, N - (o - cyanoethyl) pyrrolidine, N - o - cyanoethylethyleneimine, N,N1 - di - (o - cyanoethyl) - 4,41 - diamino - dicyclohexylmethane, N - (o - cyanoethyl) - 3 - (o - aminoethyl) - camphenilane, N,N1 - di - (o - cyanoethyl - cyanomethyl) - 4,41 - diaminodicyclohexylmethane, N,N1 - di - (o - cyanoethylhydroxylethyl) - 4,41 - diaminodicyclohexylmethane, N,N1 - di - (o - cyanobutyl) - 4,41 - diaminodicyclohexylmethane, 4,41 - diaminodicyclohexylmethane substituted on each N atom by a group -CH2.CH2.CH2.NH.CH2-CH2-CN, N,N1 - di - (a - cyanobutyl) - 4,41 - diaminodicyclohexylmethane, N,N1 - di - (a - cyanoethyl) - 4,41 - diaminodicyclohexylmethane, N - (o - cyanoethyl) cyclohexylamine, N,N1 - di - (o - cyanoethyl) - 1,4 - or - 1,2 - diaminocyclohexane, N - (o - cyanoethyl) - 2 - cyclohexyl - cyclohexylamine, N - (o - cyanoethyl) - 1,2,3,4 - tetrahydro - 1 - or - 2 - naphthylamine, N,N1 - di - (o - cyanoethyl) - 4,41 - diamino - dicyclohexylamine, N - (o - cyanoethyl) hexamethyleneimine and N-(a - or o -cyanoethyl) piperidine.ALSO:The inhibition of gas-fading of dyeings on cellulose derivative textiles is effected by incorporating in the composition from which the fibres are spun a colourless, water-insoluble, fully saturated, from 3 to 7 membered mononitrogen heterocyclic compound or an amino compound having in its molecule cycloaliphatic radicals, the compound in either case having attached to nitrogen at least one cyanoalkyl group of from 1 to 10 carbon atoms. Examples of specified acid-fading inhibitors are N - (o - cyano - ethyl) - spirocyclohexylethyleneimine, N - (o - cyanoethyl) - pyrrolidine, N - w - cyanoethylethyleneimine, N.N1 - di - (o - cyanoethyl) - 4.41 - diamino - dicyclohexyl methane, N - (o - cyanoethyl) - 3 - (o - amino - ethyl) - camphenilane, N.N1 - di - (o - cyano - ethyl - cyanomethyl) - 4.41 - diaminodicyclo - hexylmethane, N.N1 - di - (o - cyanoethyl - hydroxylethyl) - 4.41 - diaminodicyclohexyl methane, N.N1 - di - (o - cyanobutyl) - 4.41 - di - aminodicyclohexylmethane, 4.41 - diaminodi - cyclohexylmethane substituted on each N atom by a group -CH2CH2.CH2.NH.CH2.CH2.CN N.N1 - di - (a - cyanobutyl) - 4.41 - diaminodi - cyclohexylmethane, N.N1 - di - (a - cyanoethyl)-4.41 - diaminodicyclohexylmethane, N - (o - cyanoethyl) - cyclohexylamine, N.N1 - di - (o - cyanoethyl) - 1.4 - or 1.2 - diaminocyclo - hexane, N - (o - cyanoethyl) - 2 - cyclohexyl - cyclohexylamine, N - (o - cyanoethyl) - 1.2.3.4 - tetrahydro - 1 - or 2 - naphthylamine, N.N1 - di(o - cyanoethyl) - 4.41 - diaminodicyclohexyl - amine, N - (o - cyanoethyl)hexamethyleneimine and N-(a or o -cyanoethyl)piperidine.ALSO:N1N1 - di - (o - cyanobutyl) - 4,41 - diaminodicyclohexylmethane is obtained by reacting 1 mol. of 4,41-diaminodicyclohexylmethane with 2 mols. of o -chlorovaleronitrile. N.N1-di-(o - cyanodecyl) - 4,41 - diaminodicyclohexylmethane is obtained by reacting 1 mol. of 4,41-diaminodicyclohexylmethane with 2 mols. of o -bromo-o 1-cyanodecane. The compound 4,41 - diaminodicyclohexylmethane substituted on each N atom by a group -CH2.CH2.CH2. NH.CH2.CH2.CH is obtained by reacting 1 mol. of 4,41-diaminodicyclohexylmethane with 2 mols. of acrylonitrile, reducing the nitrile thus obtained to the corresponding amine and reacting 1 mol. of the amine with 2 mols. of acrylonitrile. The water-soluble formaldehydebisulphite compound of N.N1-(o -cyanoethyl)-4,41 - diaminodicyclohexylmethane is obtained by treating 1 mol. of the cyanoalkylamine with 2 mols. of sodium hydrogen sulphite and 2 mols. of formaldehyde.
GB8358/53A 1952-04-03 1953-03-26 Improvements in the dyeing of textile materials of an organic derivative of cellulose Expired GB725353A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB19839A DE925042C (en) 1952-04-03 1952-04-03 Process for improving the exhaust gas fastness of colored cellulose esters and ethers

Publications (1)

Publication Number Publication Date
GB725353A true GB725353A (en) 1955-03-02

Family

ID=6960168

Family Applications (2)

Application Number Title Priority Date Filing Date
GB8358/53A Expired GB725353A (en) 1952-04-03 1953-03-26 Improvements in the dyeing of textile materials of an organic derivative of cellulose
GB24110/53A Expired GB742029A (en) 1952-04-03 1953-09-01 Improvements in dyeing and printing textile materials of organic derivatives of cellulose

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB24110/53A Expired GB742029A (en) 1952-04-03 1953-09-01 Improvements in dyeing and printing textile materials of organic derivatives of cellulose

Country Status (4)

Country Link
US (1) US2813773A (en)
DE (4) DE925042C (en)
FR (3) FR1077680A (en)
GB (2) GB725353A (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2888314A (en) * 1955-01-27 1959-05-26 Rohm & Haas Textile material and inhibition of acid-fading dyes thereon
DE1131640B (en) * 1958-11-17 1962-06-20 Ciba Geigy Process for dyeing structures made of cellulose triacetate
DE1119817B (en) * 1959-03-25 1961-12-21 Basf Ag Process for dyeing and printing structures that consist entirely or in part of synthetic, linear, fiber-forming polyesters
US8318309B2 (en) * 2007-02-07 2012-11-27 Air Products And Chemicals, Inc. Benzylated aminopropylated alkylenediamines and uses thereof
US8198395B2 (en) * 2007-02-07 2012-06-12 Air Products And Chemicals, Inc. Alkylated aminopropylated ethylenediamines and uses thereof
US7993751B2 (en) * 2007-02-07 2011-08-09 Air Products And Chemicals, Inc. Alkylated aminopropylated methylene-di-(cyclohexylamine) and uses thereof

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR745039A (en) * 1933-05-01
US2017119A (en) * 1931-02-11 1935-10-15 Celanese Corp Treatment of textile and other materials
FR835993A (en) * 1938-03-31 1939-01-06 Improvements in the treatment of textiles and similar products
US2529935A (en) * 1947-10-15 1950-11-14 Gen Aniline & Film Corp Acid-fading inhibition using certain 1, 4-diaryl piperazines
US2539212A (en) * 1948-11-05 1951-01-23 Gen Aniline & Film Corp Gas fading inhibitors for cellulose derivative dyes

Also Published As

Publication number Publication date
FR68702E (en) 1958-06-09
DE953428C (en) 1956-11-29
US2813773A (en) 1957-11-19
FR1087963A (en) 1955-03-02
DE960001C (en) 1957-03-14
DE925042C (en) 1955-03-10
GB742029A (en) 1955-12-14
FR1077680A (en) 1954-11-10
DE939206C (en) 1956-02-16

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