GB927404A - Water-soluble dyestuffs containing hydroxy alkyl groups - Google Patents

Water-soluble dyestuffs containing hydroxy alkyl groups

Info

Publication number
GB927404A
GB927404A GB3943159A GB3943159A GB927404A GB 927404 A GB927404 A GB 927404A GB 3943159 A GB3943159 A GB 3943159A GB 3943159 A GB3943159 A GB 3943159A GB 927404 A GB927404 A GB 927404A
Authority
GB
United Kingdom
Prior art keywords
group
acid
copper phthalocyanine
reacting
methyl
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
GB3943159A
Inventor
Robert Norman Heslop
Frederick Andrew Waite
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.)
Imperial Chemical Industries Ltd
Original Assignee
Imperial Chemical Industries Ltd
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 Imperial Chemical Industries Ltd filed Critical Imperial Chemical Industries Ltd
Priority to GB3943159A priority Critical patent/GB927404A/en
Publication of GB927404A publication Critical patent/GB927404A/en
Expired legal-status Critical Current

Links

Classifications

    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06PDYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
    • D06P1/00General 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
    • D06P1/0056Dyeing with polymeric dyes involving building the polymeric dyes on the fibres
    • D06P1/0064Dyeing with polymeric dyes involving building the polymeric dyes on the fibres by using reactive polyfunctional compounds, e.g. crosslinkers

Landscapes

  • Engineering & Computer Science (AREA)
  • Structural Engineering (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)

Abstract

4-Amino-o -[N- (2:3:4:5:6-pentahydroxy-n-hexyl) -N- methylamino]- acetophenone is made by reacting acetanilide with chloracetyl chloride, condensing the 4-acetylamino-o -chloroacetophenone obtained with N-methyl glucamine and hydrolysing the acetyl group with dilute aqueous hydrochloric acid. 4-Aminobenzene sulphone-N- methyl-N-b -[N1-(2:3:4:5:6- pentahydroxyn -hexyl)-N1-methylamino]ethylamide is made by chlorosulphonating acetanilide, treating with N-methyl glucamine and hydrolysing the acetyl group. 4-Amino-o -[N1- (2:3:4:5:6-pentahydroxy-n-hexyl) -N1-methylamino]- N-ethyl-acetanilide is made by reacting 4-nitro-N-ethylaniline with chloracetyl chloride, treating the product with N-methyl-glucamine and reducing the nitro group with iron filings.ALSO:The invention comprises water-soluble dyes which contain at least one sulphonic acid or carboxylic acid group and at least one group of the formula <FORM:0927404/IV(a)/1> wherein A is a substituted or unsubstituted alkylene radical, R11 is hydrogen or a substituted or unsubstituted alkyl radical and Y is an alkyl radical containing at least two hydroxy groups, in which the group of Formula I is attached to a carbon atom of an aryl ring through one of the linking groups <FORM:0927404/IV(a)/2> and <FORM:0927404/IV(a)/3> where R is hydrogen or substituted or unsubstituted alkyl. The dyes specified are of the monoazo, polyazo, metallized azo, nitro, anthraquinone and phthalocyanine series. Alkyl radicals specified for group Y include dihydroxypropyl and -butyl, trihydroxy-butyl and -pentyl and pentahydroxyhexyl. The dyes are made by reacting an amine of the formula <FORM:0927404/IV(a)/4> with a water-soluble dye containing at least one sulphonic or carboxylic acid group and at least one group -A-Z attached via <FORM:0927404/IV(a)/5> or <FORM:0927404/IV(a)/6> or at least one group -CH2CH2OW attached via <FORM:0927404/IV(a)/7> or at least one vinyl group attached via <FORM:0927404/IV(a)/8> where A, R, R11 and Y are as above, Z is chlorine or bromine and W is the residue of a mono- or polybasic organic or inorganic acid. Azo dyes are also made by coupling a diazotized aromatic amine with a coupling component, at least one of the reactants containing a sulphonic or carboxylic acid group and at least one containing a group of Formula I above. Examples are given. The dyes dye cellulose textile materials in a variety of shades, if desired in conjunction with a treatment with formaldehyde and/or a resin-forming intermediate and an acid-liberating catalyst and a subsequent heat treatment at above 100 DEG C. Resin-forming intermediates mentioned are methylol-melamine, methylolurea, acetals, isocyanates, dimethylol cyclic ethylene urea, dimethylolglyoxal urea, dimethylol cyclic propylene urea, tetramethylol acetylene diurea and methyloltriazines. Acid-liberating catalysts mentioned are ammonium dihydrogen phosphate, ammonium thiocyanate, zinc chloride, magnesium chloride, zinc nitrate and 2-methyl-2-aminopropanol hydrochloride. The Provisional Specification refers to watersoluble dyes containing at least one group of the formula <FORM:0927404/IV(a)/9> where X is <FORM:0927404/IV(a)/100> A is a substituted or unsubstituted alkylene radical, R, R1 and R11 are each hydrogen or substituted or unsubstituted alkyl, Y is an alkyl or cycloalkyl radical containing at least two hydroxy groups and n and m are each 1 or 2. Di-(b -chloroethylsulphamyl) -1:4 - bis-(211 - methoxy-41-phenoxyanilino)anthraquinone-disulphonic acid is made by reacting b -chloroethylamine hydrochloride with sulphochlorinated 1:4-bis-(211-methoxy-41-phenoxyanilino)anthraquinone. 3-[31-(b -sulphatoethylsulphonyl)phenylsulpamyl]copper phthalocyanine sulphonic acid and 3-(31-b -sulphatoethylsulphonylmethyl-41 -methylphenylaminosulphonyl)-copper phthalocyanine sulphonic acid are made by reacting sulphochlorinated copper phthalocyanine with 3-aminophenylb -hydroxyethyl sulphone hydrochloride and 5-amino-2-methylbenzyl-p-hydroxyethylsulphone respectively and esterifying the products with sulphuric acid. Copper phthalocyanine-3-sulphonic acid sulphonamide sulphon-b -chlorethylamide is made by reacting sulphochlorinated copper phthalocyanine with b -chloroethylamine and ammonia. Copper phthalocyanine-4-sulphonic acid-sulphon-N-methyl-N-pentahydroxyhexyl amide-sulphon-b -chloroethylamide and copper phthalocyanine-4-sulphonic acid sulphon-b -hydroxyethylamide sulphon-b -chloroethylamide are made by treating copper phthalocyanine tetra-4-sulphonic acid with chlorosulphonic acid and reacting the sulphochloride obtained with b -chloroethylamino and respectively N-methyl-glucamine or monoethanolamine. Copper phthalocyanine-4-sulphonic acid-sulphonamide-sulphon-b :g -dichloropropyl amide and the corresponding -g -chloro-b -hydroxypropylamide are made by reacting the sulphochloride obtained from copper phthalocyanine tetra-4-sulphonic acid and chlorosulphonic acid with ammonia and respectively b :g -dichloropropylamine or g -chloro-b -hydroxypropylamine. Specifications 587,467, 712,037, 733,471, 7490,533, 768,241, 774,819, 776,265, 779,781, 779,818, 787,986, 826,689, 830,847, 837,750, 852,960, 858,183, 868,492, 870,047, 881,737, 882,750, 885,814, 885,681, 886,379, 887,870 and 891,248 are referred to.
GB3943159A 1959-11-20 1959-11-20 Water-soluble dyestuffs containing hydroxy alkyl groups Expired GB927404A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB3943159A GB927404A (en) 1959-11-20 1959-11-20 Water-soluble dyestuffs containing hydroxy alkyl groups

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB3943159A GB927404A (en) 1959-11-20 1959-11-20 Water-soluble dyestuffs containing hydroxy alkyl groups

Publications (1)

Publication Number Publication Date
GB927404A true GB927404A (en) 1963-05-29

Family

ID=10409501

Family Applications (1)

Application Number Title Priority Date Filing Date
GB3943159A Expired GB927404A (en) 1959-11-20 1959-11-20 Water-soluble dyestuffs containing hydroxy alkyl groups

Country Status (1)

Country Link
GB (1) GB927404A (en)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3426016A (en) * 1962-10-03 1969-02-04 Hoechst Ag Basic phthalocyanine dyestuffs
US6332918B1 (en) 1998-02-17 2001-12-25 Avecia Limited Phthalocyanine compounds for ink-jet printing
CN117005056A (en) * 2023-08-22 2023-11-07 江苏新视界先进功能纤维创新中心有限公司 Polymer coloring method, spinning color paste, spinning solution and colored fiber

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3426016A (en) * 1962-10-03 1969-02-04 Hoechst Ag Basic phthalocyanine dyestuffs
US6332918B1 (en) 1998-02-17 2001-12-25 Avecia Limited Phthalocyanine compounds for ink-jet printing
CN117005056A (en) * 2023-08-22 2023-11-07 江苏新视界先进功能纤维创新中心有限公司 Polymer coloring method, spinning color paste, spinning solution and colored fiber

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