GB566741A - Manufacture of sulphur-containing dyestuffs - Google Patents

Manufacture of sulphur-containing dyestuffs

Info

Publication number
GB566741A
GB566741A GB908743A GB908743A GB566741A GB 566741 A GB566741 A GB 566741A GB 908743 A GB908743 A GB 908743A GB 908743 A GB908743 A GB 908743A GB 566741 A GB566741 A GB 566741A
Authority
GB
United Kingdom
Prior art keywords
thiourea
metal
chloride
phthalocyanine
heated
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
GB908743A
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 GB908743A priority Critical patent/GB566741A/en
Publication of GB566741A publication Critical patent/GB566741A/en
Expired legal-status Critical Current

Links

Classifications

    • 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
    • C09B47/00—Porphines; Azaporphines
    • C09B47/04—Phthalocyanines abbreviation: Pc
    • C09B47/08—Preparation from other phthalocyanine compounds, e.g. cobaltphthalocyanineamine complex
    • C09B47/24—Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
    • C09B47/26—Amide radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Coloring (AREA)

Abstract

Sulphur-containing dyestuffs, capable of dyeing cotton from a sodium sulphide vat, are obtained by heating a sulphonyl chloride of a metal-containing or metal-free phthalocyanine with a thioamide containing at least one -CS.NHR group, wherein R may represent H, alkyl (including allyl) or aryl. Specified sulphonyl chlorides are copper phthalocyanine-tetra-(4)-sulphonyl chloride, copper phthalocyanine-tri-(4)-sulphonyl chloride, metal-free phthalocyanine-tri-sulphonyl chloride and a copper phthalocyanine polysulphonyl chloride obtained by the action of phosphorus pentachloride in nitrobenzene at 100-110 DEG C. on a sulphonation product obtained by heating copper phthalocyanine with 25 per cent oleum for 12 hours at 70 DEG C. and then for 2 hours at 85 DEG C. Specified thioamides are thioacetamide, thioacetanilide, thiobenzamide, thiobenzanilide, phenyldithiobiuret, thiourea, N-allyl-thiourea, N - methyl - thiourea, N : N1 - dimethyl - thiourea and N : N1 : N1 - trimethyl - thiourea. In examples: (1) copper phthalocyanine-tetra-(4)-sulphonyl chloride (obtainable by heating tetra-potassium copper phthalocyanine - tetra - (4) - sulphonate with phosphorus pentachloride in nitrobenzene) is heated for 2 hours with thiourea at 170-175 DEG C.; (2) the thiourea in (1) is replaced by thiobenzanilide; (3) metal-free phthalocyanine-trisulphonyl chloride (obtainable by heating with phosphorus pentachloride in nitrobenzene the sodium salt of the metal-free phthalocyanine trisulphonic acid obtained by direct sulphonation of metal-free phthalocyanine) is heated for 2 hours with thiourea at 170-175 DEG C.; (4) the thiourea in (3) is replaced by phenyldithiobiuret; (5), (6) and (7), metal-free phthalocyanine-trisulphonyl chloride is heated for 1/2 hour with (5) N-methyl-thiourea, (6) N : N1 - dimethyl - thiourea, (7) N : N1 : N1-trimethyl-thiourea at 120-125 DEG C.; (8) metal-free phthalocyanine-trisulphonyl chloride is heated for 1/4 hour with thioacetanilide at 110-115 DEG C.; (9) metal-free phthalocyanine trisulphonyl chloride is heated for 1/4 hour with thioacetamide at 130-135 DEG C.; (10) copper phthalocyanine polysulphonyl chloride (obtained as above) is heated for 1 hour with thiourea at 170-175 DEG C. N-Allyl-thiourea is obtained by the action of ammonia on allyl isothiocyanate.
GB908743A 1943-07-07 1943-07-07 Manufacture of sulphur-containing dyestuffs Expired GB566741A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB908743A GB566741A (en) 1943-07-07 1943-07-07 Manufacture of sulphur-containing dyestuffs

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB908743A GB566741A (en) 1943-07-07 1943-07-07 Manufacture of sulphur-containing dyestuffs

Publications (1)

Publication Number Publication Date
GB566741A true GB566741A (en) 1945-01-11

Family

ID=9865100

Family Applications (1)

Application Number Title Priority Date Filing Date
GB908743A Expired GB566741A (en) 1943-07-07 1943-07-07 Manufacture of sulphur-containing dyestuffs

Country Status (1)

Country Link
GB (1) GB566741A (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1544470B1 (en) * 1964-07-18 1970-01-22 Ugine Kuhlmann Process for the production of dyes and their use

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1544470B1 (en) * 1964-07-18 1970-01-22 Ugine Kuhlmann Process for the production of dyes and their use

Similar Documents

Publication Publication Date Title
GB566741A (en) Manufacture of sulphur-containing dyestuffs
US2223042A (en) Method of making 1,1-dithio bis arylenethiazoles
GB457477A (en) Manufacture of thiazole derivatives
GB816657A (en) Process for the production of sulphur dyestuffs of the phthalocyanine series
GB588696A (en) Sulphur-containing dyestuffs
GB558433A (en) New anthraquinone dyestuffs
US2453953A (en) Process for preparing sulfur-containing phthalocyanine dyestuffs
GB566740A (en) Manufacture of sulphur-containing dyestuffs
GB462693A (en) Process for the manufacture of new acid wool dyestuffs of the anthraquinone series
SU403655A1 (en) In PTB
US2265319A (en) Manufacture of dithio-bis-thiazoles
GB792018A (en) Sulphur containing dyestuffs of the phthalocyanine series
DE615526C (en) Process for the preparation of 2-aminoarylene thiazoles
GB562755A (en) Manufacture of new colouring matters
GB1512775A (en) Process for the preparation of aminonitrophenols
GB455991A (en) Process for the manufacture of a chrysene monosulphonic acid
GB795142A (en) Process for the preparation of salts of dithiocarbamic acids, having a low water solubility
GB515637A (en) Process for the manufacture of phthalocyanine sulphonic acid chlorides
GB710614A (en) Improvements relating to thiadiazole sulfonamides and the preparation thereof
SU101714A1 (en) The method of obtaining 2,2'-diochi-5,5'-dichlorodiphenylsulfide
GB629488A (en) Process for the preparation of water-soluble dyestuffs of the phthalo-cyanine series
DE649998C (en) Process for the preparation of anthraquinone dyes
GB182084A (en) Manufacture of 2-oxy-1-aryl-naphthylamines
GB952497A (en) Anthraquinone sulphonchloride manufacturing process
GB791498A (en) Manufacture of a vat dyestuff containing sulphur