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GB1022756A - Substituted benzoyl chlorides and textile auxiliaries prepared therefrom - Google Patents

Substituted benzoyl chlorides and textile auxiliaries prepared therefrom

Info

Publication number
GB1022756A
GB1022756A GB2608163A GB2608163A GB1022756A GB 1022756 A GB1022756 A GB 1022756A GB 2608163 A GB2608163 A GB 2608163A GB 2608163 A GB2608163 A GB 2608163A GB 1022756 A GB1022756 A GB 1022756A
Authority
GB
United Kingdom
Prior art keywords
acid
formula
amino
acids
dyes
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
GB2608163A
Inventor
James F Feeman
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.)
Crompton and Knowles Corp
Original Assignee
Crompton and Knowles Corp
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
Priority to US38733A priority Critical patent/US3098096A/en
Priority to US256784A priority patent/US3261658A/en
Application filed by Crompton and Knowles Corp filed Critical Crompton and Knowles Corp
Priority to GB2608163A priority patent/GB1022756A/en
Priority to DE19631444611 priority patent/DE1444611A1/en
Publication of GB1022756A publication Critical patent/GB1022756A/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
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
    • D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
    • D06M13/1845—Aromatic mono- or polycarboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00—Sulfones; Sulfoxides
    • C07C317/44—Sulfones; Sulfoxides having sulfone or sulfoxide groups and carboxyl groups bound to the same carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/16—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms condensed with carbocyclic rings or ring systems
    • C07D249/22—Naphthotriazoles
    • C07D249/24—Naphthotriazoles with stilbene radicals directly attached in position 2
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B43/00—Preparation of azo dyes from other azo compounds
    • C09B43/12—Preparation of azo dyes from other azo compounds by acylation of amino groups
    • C09B43/124—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters
    • C09B43/132—Preparation of azo dyes from other azo compounds by acylation of amino groups with monocarboxylic acids, carbamic esters or halides, mono- isocyanates, or haloformic acid esters having the carboxylic group directly attached to an aromatic carbocyclic ring
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B62/00—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves
    • C09B62/44—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring
    • C09B62/503—Reactive dyes, i.e. dyes which form covalent bonds with the substrates or which polymerise with themselves with the reactive group not directly attached to a heterocyclic ring the reactive group being an esterified or non-esterified hydroxyalkyl sulfonyl or mercaptoalkyl sulfonyl group, a quaternised or non-quaternised aminoalkyl sulfonyl group, a heterylmercapto alkyl sulfonyl group, a vinyl sulfonyl or a substituted vinyl sulfonyl group, or a thiophene-dioxide group
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
    • D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
    • D06M13/272—Unsaturated compounds containing sulfur atoms
    • D06M13/278—Vinylsulfonium compounds; Vinylsulfone or vinylsulfoxide 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
    • D06P1/651—Compounds without nitrogen
    • D06P1/65168—Sulfur-containing compounds
    • D06P1/65193—Compounds containing sulfite or sulfone groups

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Coloring (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Fibre-reactive dyes have the formula <FORM:1022756/C4-C5/1> wherein R is H, Me or Et and Z is in the n- or p-position and is <FORM:1022756/C4-C5/2> A being a dye attached through a functional group from which H has been displaced and B being the residue of a dye capable of forming a heterocyclic system upon condensation with a carbonyl chloride. The dyes are made by reacting compounds of the above formula in which Z is -COCl with dyes providing the residues A or B. In examples, products have the following formulae <FORM:1022756/C4-C5/3> or are prepared by reacting the chloroethyl-sulphonylbenzoyl chloride with the copper complex of 2 - amino - 1 - phenol - 4 - sulphonic acid --> 6 - amino - 1 - naphtol - 3 - sulphonic acid, with a 3-nitro-4-chlorobenzenesulphonic acid/p-phenylenediamine condensate or with compounds of formulae <FORM:1022756/C4-C5/4> The acid chloride starting material may be reacted successively with two different dyes; a specified product is the copper complex of the compound of formula <FORM:1022756/C4-C5/5>ALSO:The invention comprises m- and p-compounds of formula <FORM:1022756/C2/1> wherein R is H, Me or Et. In examples, the (m- and p-) 2-hydroxyethylmercaptobenzoic acids are respectively obtained from the mercaptobenzoic acids with ethylene chlorohydrin and oxidized with NaClO to the 2-hydroxyethylsulphonylbenzoic acids (a) which are reacted with thionyl chloride to give the 2-chloroethylsulphonylbenzoyl chlorides; the intermediates (a) are alternatively obtained by reacting sodium sulphonylbenzoic acids (from the reduction of chlorosulphonylbenzoic acids) with ethylene oxide or chlorohydrin and it is also stated that they may be converted to the 2-chloroethylsulphonylbenzoic acids with conc. HCl. The compounds of the invention may be reacted with textile auxiliaries to replace the chlorocarbonyl groups by <FORM:1022756/C2/2> In examples, A is attached by NH derived from NH2 in 7-amino-1-naphthol-3-sulphonic acid, the 5-NH2 in 2,5-diaminobenzenesulphonic acid or NH2 in the optical brightener of formula <FORM:1022756/C2/3> while B is attached by <FORM:1022756/C2/4> derived from the two NH2 groups in 5,6-diamino-1-naphthol-3-sulphonic acid.ALSO:Textiles are dyed by a process in which azo-dyes are formed on the material, wherein a m- or pcompound of formula <FORM:1022756/D1-D2/1> in which R is H, Me or Et and A is the residue of an azo-dye intermediate, is reacted with the fibre to eliminate HCl and the dye developed with a suitable coupling agent. In example 4, the fibre-reactive compound has the formula <FORM:1022756/D1-D2/2> and after impregnating spun rayon, it is developed with diazonium salts of metanilic acid, 4-methoxymetanilic acid or 5-amino-6-methoxynaphthalene-2-sulphonic acid. In example 8, the fibre-reactive compound has the formula <FORM:1022756/D1-D2/3> and after impregnating spun rayon it is diazotised and coupled with barbituric acid, 3-methyl-1-p-sulphophenyl-2-pyrazol-5-one, resorcinol, 3-hydroxy-2-naphthanilide, 6-amino-1-naphthol-3-sulphonic acid or 8-amino-1-naphthol-3, 6-disulphonic acid. <FORM:1022756/D1-D2/4> in which the NH2 is substituted by a p-2-chloroethylsulphonylbenzoyl group reacts ink cellulosic fibres such as cotton and viscose rayon, imparting optical brightness thereto.
GB2608163A 1960-06-27 1963-07-01 Substituted benzoyl chlorides and textile auxiliaries prepared therefrom Expired GB1022756A (en)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US38733A US3098096A (en) 1960-06-27 1960-06-27 3-and 4-(2-chlorethylsulfonyl)-benzoyl chloride
US256784A US3261658A (en) 1960-06-27 1962-12-10 Process of reacting chloroethyl-sulfonyl benzoyl chloride compounds with textile auxiliaries and reacting said auxiliaries with textile fibers
GB2608163A GB1022756A (en) 1963-07-01 1963-07-01 Substituted benzoyl chlorides and textile auxiliaries prepared therefrom
DE19631444611 DE1444611A1 (en) 1963-07-01 1963-07-13 Dye and its manufacturing process

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB2608163A GB1022756A (en) 1963-07-01 1963-07-01 Substituted benzoyl chlorides and textile auxiliaries prepared therefrom
DEC0030440 1963-07-13

Publications (1)

Publication Number Publication Date
GB1022756A true GB1022756A (en) 1966-03-16

Family

ID=25969709

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2608163A Expired GB1022756A (en) 1960-06-27 1963-07-01 Substituted benzoyl chlorides and textile auxiliaries prepared therefrom

Country Status (2)

Country Link
DE (1) DE1444611A1 (en)
GB (1) GB1022756A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3029383A1 (en) * 1980-08-01 1982-03-18 Hoechst Ag, 6000 Frankfurt WATER-SOLUBLE, FIBER-REACTIVE COMPOUNDS, THEIR PRODUCTION AND USE AND NEW (BETA) -CHLORAETHYLSULFONYLMETHYL-BENZOESAIC HALOGENIDES AND THEIR USE AS FIBER-REACTIVE ANCHORS

Also Published As

Publication number Publication date
DE1444611A1 (en) 1969-05-29

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