GB284247A - Process for the manufacture of water-insoluble azo dyestuffs - Google Patents

Process for the manufacture of water-insoluble azo dyestuffs

Info

Publication number
GB284247A
GB284247A GB2456/28A GB245628A GB284247A GB 284247 A GB284247 A GB 284247A GB 2456/28 A GB2456/28 A GB 2456/28A GB 245628 A GB245628 A GB 245628A GB 284247 A GB284247 A GB 284247A
Authority
GB
United Kingdom
Prior art keywords
xylidine
acid
bluish
red
naphthalide
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
GB2456/28A
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.)
IG Farbenindustrie AG
Original Assignee
IG Farbenindustrie 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 IG Farbenindustrie AG filed Critical IG Farbenindustrie AG
Publication of GB284247A publication Critical patent/GB284247A/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
    • C09B29/00—Monoazo dyes prepared by diazotising and coupling
    • C09B29/10—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group
    • C09B29/18—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides
    • C09B29/20—Monoazo dyes prepared by diazotising and coupling from coupling components containing hydroxy as the only directing group ortho-Hydroxy carbonamides of the naphthalene series

Landscapes

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

Abstract

284,247. I. G. Farbenindustrie Akt.- Ges. Jan. 25, 1927, [Convention date]. Monoazo dyes.-Azo dyes are produced in substance or upon the fibre by coupling with an arylide of 2: 3-oxynapthoic acid a diazotized amine of the formula in which R is hydrogen or alkyl and R1 is benzoyl or substituted benzoyl. The following examples are specified :-(1) Cotton is impregnated with a solution of the a-naphthalide of 2 :-3-oxy- -naphthoic acid and developed with a diazo solution of benzoylamino-as-m-xylidine (NH2 : CH3 :- CH3: NH.CO.C6H5=1: 2: 4: 5) to produce a bluish-red dyeing. (2) The 4-chlora-2-toluidine with the corresponding methylbenzoylamino-asm-xylidine similarly yield a bluish-red dyeing, and with dichlorbenzoylamino-as-m-xylidine a yellower bluish-red. Specifications 6379/12; 17279/13, [Class 15 (ii), Dyeing, Processes &c. for]; and 254,578 are referred to. Benzoylamino-as-m-xylidine (NH2 : CH3 : CH3 : NH.CO.C6H5=1 : 2 : 4 5) is obtained by benzoylation of as-m-xylidine with benzoyl chloride in presence of an acid binding agent, followed by nitration and reduction of the nitro group. Dichlorbenzoylamino - as - m - xylidine (NH2 : CH3 : CH3 : NH.CO.C6H3.Cl2 = 1: 2 : 4 : 5) is similarly obtained using 2 : 4-dichlorbenzoyl chloride as benzoylating agent. Methylbenzoylamino - as - m - xylidine (NH2: CH3 : CH3 : N = 1 : 2 : 4 : 5) is ob- @@@@@@@@@@@@@ tained by interaction of as-m-xylidine with ptoluenesulphonic chloride in presence of an acid binding agent, followed by methylation of the NH group with dimethyl sulphate, saponification with sulphuric acid, benzoylation, nitration, and reduction. The Specification as open to inspection under Sect. 91 (3) (a) comprises also the production of the corresponding dyestuffs in which R is aralkyl and those in which R1 is hydrogen, alkyl, aralkyl, or an arylsulphonic acid group, and contains examples in which (a) the #-naphthalide replaces the a-naphthalide in example (1), and (b) material is dyed bluish red by impregnation with a solution of the m-nitranilide of 2 : 3-oxynaphthoic acid and development with a diazo solution of the corresponding amine in which R is CH3 and R1 is SO2.C6H4.CH3. This subject-matter does not appear in the Specification as accepted.
GB2456/28A 1927-01-25 1928-01-25 Process for the manufacture of water-insoluble azo dyestuffs Expired GB284247A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DE284247X 1927-01-25

Publications (1)

Publication Number Publication Date
GB284247A true GB284247A (en) 1929-04-25

Family

ID=6050855

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2456/28A Expired GB284247A (en) 1927-01-25 1928-01-25 Process for the manufacture of water-insoluble azo dyestuffs

Country Status (1)

Country Link
GB (1) GB284247A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2739981A (en) * 1952-08-26 1956-03-27 American Home Prod Diamines and salts thereof
US3242213A (en) * 1962-09-11 1966-03-22 Monsanto Co Diamides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2739981A (en) * 1952-08-26 1956-03-27 American Home Prod Diamines and salts thereof
US3242213A (en) * 1962-09-11 1966-03-22 Monsanto Co Diamides

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